Supporting Information
|
|
- Πύρρος Μπουκουβαλαίοι
- 5 χρόνια πριν
- Προβολές:
Transcript
1 Supporting Information Wiley-VCH Weinheim, Germany
2 Catalytic, Enantioselective Crossed Aldehyde Ketone Benzoin Cyclization Hiroshi Takikawa, Yoshifumi Hachisu, Jeffrey W. Bode, and Keisuke Suzuki * [*] Department of Chemistry, Tokyo Institute of Technology, SRST JST Agency, okayama, guro-ku, Tokyo (Japan) [ Present address] Department of Chemistry and Biochemistry, University of California, Santa Barbara, CA , (USA) Experimental Section General thods: All reactions utilizing air- or moisture-sensitive reagents were performed in dried glassware under an atmosphere of dry Ar and N 2. Substrates 3, 14, 15 were prepared by our previously reported methods. [1] Substrates 8 13 were prepared by literature procedures. [2] Catalysts 5, 7, 2a, 2b were prepared by literature methods. [3,4] Ethereal solvents (anhydrous; Kanto Chemical Co., Inc.) were used as received. t-buh was distilled prior to use. CH 2 Cl 2 was distilled successively from P 2 5 and CaH 2, and stored over 4A molecular sieves. DBU was distilled from Ba. Kt-Bu was purified by sublimation. Et 3 N was distilled from KH. ther reagents were used without further purification. Thin layer chromatography (TLC) was performed on rck precoated plates (silica gel 60 F254, Art 5715, 0.25 mm) and were visualized by fluorescence quenching under UV light or by staining with phosphomolybdic acid. Silica-gel preparative thin-layer chromatography (PTLC) was [1] a) J. W. Bode, T. Matsuura, Y. Hachisu, K. Suzuki, Tetrahedron Lett. 2003, 44, ; b) T. Matsuura, J. W. Bode, Y. Hachisu, K. Suzuki, Synlett 2003, 11, ; c) Y. Hachisu, J. W. Bode, K. Suzuki, J. Am. Chem. Soc. 2003, 125, [2] Y. Hachisu, J. W. Bode, K. Suzuki, Adv. Synth. Catal. 2004, 346, [3] R. L. Knight, F. J. Leeper, Tetrahedron Lett. 1997, 38, [4] R. L. Knight, F. J. Leeper, J. Chem. Soc., Perkin Trans , Page 1
3 performed using plates prepared from rck Kieselgel 60 PF 254 (Art 7747). Column chromatography was performed on E. rck Silica Gel 60 ( sh) using a forced flow of bar. lting point (m.p.) determinations were performed using a Yanaco MP-S3 instrument and are uncorrected. 1 H NMR and 13 C NMR were measured on a JEL JMN Lambda-300 or Lambda-400 spectrometer. Chemical shifts are expressed in parts per million (PPM) downfield from internal tetramethylsilane (δ = 0), and coupling constants are reported as hertz (Hz). Splitting patterns are indicated as follows: br, broad; s, singlet; d, doublet; t, triplet; q, quartet; m, multiplet. Infrared (IR) spectra were recorded on a Jasco IRA-202 spectrophotometer and are reported as wavenumbers (cm 1 ). High performance liquid chromatography (HPLC) analyses were performed using a JASC C-2060 plus for intelligent column thermostat, UV-2077 plus for intelligent UV/VIS detector, PU-1580 for intelligent HPLC pump, DG for 3-line degasser and LG for ternary gradient unit. Gas chromatography (GC) analyses were performed using a SHIMADZU gas chromatograph GC-17A. Enantiomeric excesses were assessed by HPLC analysis on chiral columns, CHIRALPAK AD-H or CHIRALCEL D-H (Daicel Chemical Ind., Ltd.) and GC analysis on a capillary column, CHRMPACK Chirasil-Dex CB (GL Sciences Inc. Japan). General Procedure for Benzoin Cyclization of a Keto-aldehyde: The reaction of 3 is representative. A mixture of 3 (934 mg, 3.10 mmol) and triazolium salt 2b (101 mg, mmol) in anhydrous THF (8.75 ml) was degassed by three cycles of freeze-pumpthaw. To the mixture was added a degassed 0.40 M THF solution of DBU (0.78 ml, 0.31 mmol) dropwise at room temperature under a nitrogen atmosphere. After stirring at this temperature for 12 h, the reaction was cooled to 0 C, and water was added. The products were extracted with CH 2 Cl 2 (30 ml x 1) and EtAc (30 ml x 2). The combined organic extracts were dried over Na 2 S 4 and concentrated under reduced pressure. The residue was purified by silica-gel column chromatography (EtAc/CH 2 Cl 2 /hexane = 3/4/3) to give benzoin product 4 (92%, 99% ee) as a yellow solid. Recrystallization from EtAc gave enantiomerically pure 4 (75%, >99% ee) as Page 2
4 colorless needles. The enantiomeric excess was assessed by HPLC analysis on a chiral column: CHIRALPAK AD-H. (eluent: 2-propanol:hexane = 13:87, flow rate: 1.0 ml/min, 25 C) MM N H 4 Spectroscopic data of 4: colorless solid, m.p C; 1 H NMR (400 MHz, CDCl 3 ) δ 7.75 (dd, 1 H, J = 6.6, 2.4 Hz), (m, 2 H), 5.37 (d, 1 H, J = 7.1 Hz), 5.34 (d, 1 H, J = 7.1 Hz), 3.53 (s, 3 H), 2.99 (dd, 1 H, J = 16.3, 6.4 Hz), (m, 1 H), 2.58 (bs, 1 H), (m, 3 H), 1.64 (td, 1 H, J = 14.2, 3.2 Hz); 13 C NMR (100 MHz, CDCl 3 ) δ 195.1, 171.1, 154.0, 153.3, 133.3, 131.5, 122.9, 120.4, 117.8, 113.6, 94.4, 67.1, 56.4, 28.9, 22.3, 17.8; IR (KBr) 3484, 2957, 1702, 1665, 1576, 1264, 1155, 1012, 911, 801 cm 1 ; Anal. Calc d for C 16 H 15 N 5 : C, 63.78; H, 5.02; N, 4.65, Found: C, 63.74; H, 5.25; N, 4.43; HPLC (CHIRALPAK AD-H, eluent: 2-propanol:hexane = 13:87, flow rate: 1.0 ml/min, 25 C): (R)-4: t 1 = 21.4 min; (S)-4: t 2 = 32.9 min; [α] 21 D (CHCl 3, c 0.50) for >99% ee. MM N 26 To a solution of 4 (34.2 mg, mmol) in CH 2 Cl 2 (1.1 ml) at 0 C was added (S)- camphanic chloride (36.9 mg, mmol) and DMAP (22.2 mg, mmol). The reaction mixture was warmed to room temperature and stirred for 15 min. The reaction was quenched by addition of saturated aq NH 4 Cl solution, and the products were extracted with EtAc (10 ml x 3). The combined organic extracts were washed with brine, dried over Na 2 S 4 and concentrated under reduced pressure. The residue was purified by silica-gel preparative thin-layer chromatography (EtAc/CH 2 Cl 2 /hexane = 5/3/2) to afford (S)-camphanyl derivative 26 as colorless solid (53.0 mg, 97 %). Page 3
5 Recrystallization from EtAc gave a single crystal of 26 for the X-ray analysis. The spectroscopic data of 26; colorless solid, m.p. 167 C (decomp.); 1 H NMR (300 MHz, CDCl 3 ) δ 7.64 (dd, 1 H, J = 6.6, 2.4 Hz), (m, 2 H), 5.43 (d, 1 H, J = 7.1 Hz), 5.40 (d, 1 H, J = 7.1 Hz), 3.54 (s, 3 H), (m, 1 H), (m, 2 H), (m, 3 H), (m, 3 H), (m, 1 H), 1.03 (s, 3 H), 0.85 (s, 3 H), 0.55 (s, 3 H); 13 C NMR (75 MHz, CDCl 3 ) δ 192.5, 177.9, 171.7, 166.2, 154.1, 153.7, 134.9, 131.7, 122.3, 120.6, 118.0, 111.3, 94.8, 90.4, 76.1, 56.5, 54.8, 54.5, 30.3, 28.8, 27.7, 22.1, 18.0, 16.5, 16.0, 9.6; IR (KBr) 2970, 2943, 2879, 1782, 1751, 1689, 1654, 1574, 1485, 1281, 1207, 1109, 1057, 939, 885, 835, 768, 729 cm 1 ; Anal. Calc d for C 26 H 27 N 8 : C, 64.86; H, 5.65; N, 2.91, Found: C, 65.12; H, 5.67; N, 2.72; [α] 22 D (CHCl 3, c 1.00). CCDC contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via (or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; fax: (+44) ; or deposit@ccdc.cam.ac.uk). Spectroscopic data of chiral triazolium salts N N + N Cl 2a Spectroscopic data of 2a: light tan solid, m.p C; 1 H NMR (400 MHz, CDCl 3 ) δ 13.2 (s, 1 H), 8.11 (d, 2 H, J = 9.2 Hz), 8.07 (d, 1 H, J = 7.2 Hz), (m, 2 H), 7.20 (d, 1 H, J = 6.8 Hz), 6.94 (d, 2 H. J = 9.2 Hz), 6.38 (bd, 1 H, J = 3.6 Hz), 5.05 (s, 2 H), 5.02 (brd, 1 H, J = 3.6 Hz), 3.82 (s, 3 H), 3.10 (brs, 2 H); 13 C NMR (75 MHz, CDCl 3 ) δ 160.8, 149.0, 140.7, 139.8, 135.0, 129.4, 128.1, 127.7, , , 121.8, 114.9, 77.6, 62.1, 60.2, 55.5, 37.2; IR (KBr) 3417, 2935, 1606, 1579, 1537, 1508, 1392, 1259, 1176, 1101, 1053, 1022, 972, 837, 769, 742 cm 1 ; Anal. Calc d for C 19 H 18 ClN 3 2 : C, Page 4
6 64.13; H, 5.10; N, 11.81, Found: C, 64.06; H, 5.38; N, 11.51; [α] D (CHCl 3, c 1.00). N N + N Cl 2b Spectroscopic data of 2b: colorless solid, m.p C; 1 H NMR (300 MHz, CDCl 3 ) δ 13.5 (s, 1 H), (m, 2 H), 8.11 (bd, 1 H, J = 6.6 Hz), (m, 3 H), (m, 2 H), 7.19 (bd, 1 H, J = 6.6 Hz), 6.41 (d, 1 H, J = 4.5 Hz), 5.06 (s, 2 H), 5.03 (td, 1 H, J = 4.5, 1.5 Hz), 3.08 (brd, 1 H, J = 16.8 Hz), 3.00 (dd, 1 H, J = 16.8, 4.5 Hz); 13 C NMR (75 MHz, CDCl 3 ) δ 149.3, 141.9, 139.9, , , 130.3, 130.0, 129.5, 127.7, 125.2, 125.1, 120.2, 77.7, 62.3, 60.3, 37.2; IR (KBr) 3420, 3022, 2910, 1587, 1531, 1462, 1390, 1252, 1101, 1053, 970, 769, 744, 687 cm 1 ; Anal. Calc d for C 18 H 16 ClN 3: C, 66.36; H, 4.95; N, 12.90, Found: C, 66.10; H, 5.01; N, 12.67; [α] 23 D +316 (CHCl 3, c 1.00). Benzoin cyclization for keto-aldehyde substrates. Table 2, entry 1 8 Spectroscopic data of 8 [5] : colorless liquid; 1 H NMR (400 MHz, CDCl 3 ) δ 9.77 (t, 1 H, J = 1.6 Hz), (m, 4 H), 2.15 (s, 3 H), (m, 4 H); 13 C NMR (100 MHz, CDCl 3 ) δ 208.4, 202.2, 43.6, 43.2, 29.9, 23.1, 21.4; IR (neat) 1712 cm 1 (C=). [5] a) J. -X. Chen, K. Sakamoto, A. rita, J. tera, J. rg. Chem. 1998, 63, ; b) Ref. 2. Page 5
7 H 16 Spectroscopic data of 16 [6] : colorless liquid; 1 H NMR (400 MHz, CDCl 3 ) δ 3.94 (s, 1 H), (m, 2 H), (m, 2 H), (m, 4H), 1.41 (s, 3 H); 13 C NMR (CDCl 3 ) δ 214.4, 76.4, 42.0, 37.7, 27.8, 25.0, 23.0; IR (neat) 3483, 2939, 2866, 1714, 1450, 1373, 1185, 1120 cm 1 ; GC (CHRMPACK Chirasil-Dex CB, flow rate: 50.0 ml/min, 150 C): (S)-16: t 1 = 5.6 min; (R)-16: t 2 = 5.8 min; [α] 28 D +106 (CHCl 3, c 0.96) for 96% ee; Lit. [7] [α] 22 D (CHCl 3, c 0.962) for 95% ee. 27 Spectroscopic data of 27: colorless solid, m.p C; 1 H NMR (400 MHz, CDCl 3 ) δ (m, 4 H), (m, 8 H), 1.51 (s, 3 H), 1.12 (s, 3 H), 1.11 (s, 3 H), 1.04 (s, 3 H); 13 C NMR (100 MHz, CDCl 3 ) δ 206.3, 177.9, 166.1, 90.6, 85.2, 54.8, 54.3, 39.0, 38.9, 30.5, 28.9, 27.0, 21.83, 21.79, 16.7, 16.6, 9.6; IR (KBr) 2966, 2937, 2871, 1782, 1753, 1718, 1441, 1381, 1313, 1284, 1228, 1171, 1109, 1062, 1020, 939 cm 1 ; Anal. Calc d for C 17 H 24 5 : C, 66.21; H, 7.84, Found: C, 65.94; H, 7.89; [ ] 29 D (CHCl 3, c 1.04). CCDC contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via (or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; fax: (+44) ; or deposit@ccdc.cam.ac.uk). [6] B. K. Bettadaiah, K. N. Gurudutt, P. Srinivas, J. rg. Chem. 2003, 68, [7] T. Fujisawa, M. Watanabe, T. Sato, Chem. Lett. 1984, Page 6
8 Table 2, entry 2 9 Spectroscopic data of 9: colorless liquid; 1 H NMR (400 MHz, CDCl 3 ) δ 10.2 (s, 1 H), 7.80 (dd, 1 H, J = 7.5, 1.5 Hz), 7.51 (td, 1 H, J = 7.5, 1.5 Hz), 7.41 (td, 1 H, J = 7.5, 1.2 Hz), 7.32 (d, 1 H, J = 7.5 Hz), 3.29 (t, 2 H, J = 7.5 Hz), 2.77 (t, 2 H, J = 7.5 Hz), 2.15 (s, 3 H); 13 C NMR (100 MHz, CDCl 3 ) δ 207.5, 192.9, 143.5, , , , 131.4, 126.9, 44.8, 29.9, 27.1; IR (neat) 3073, 2942, 2899, 2747, 1708, 1694, 1599, 1574, 1362, 1207, 1191, 1158, 761 cm 1. H 17 Spectroscopic data of 17: colorless liquid; 1 H NMR (400 MHz, CDCl 3 ) δ 8.04 (d, 1 H, J = 8.0 Hz), 7.52 (dd, 1 H, J = 7.7, 7.5 Hz), 7.35 (t, 1 H, J = 7.7, 8.0 Hz), 7.26 (d, 1 H, J = 7.5 Hz), 3.87 (s, 1 H), (m, 2 H), (m, 2 H), 1.40 (s, 3 H); 13 C NMR (100 MHz, CDCl 3 ) δ 201.8, 143.4, 134.0, 129.9, 129.0, 128.0, 126.9, 73.6, 35.8, 26.8, 23.9; IR (neat) 3489, 3066, 3026, 2972, 2933, 2864, 1689, 1603, 1455, 1371, 1290, 1222, 1155, 1097, 971, 796, 742 cm 1 ; HPLC (CHIRALCEL D-H, eluent: 2- propanol:hexane = 0.25:99.75, flow rate: 1.0 ml/min, 25 C): (R)-17: t 1 = 22.2 min; (S)- 17: t 2 = 26.3 min; [α] 30 D (CHCl 3, c 2.00) for 96% ee; Lit. [8] [α] D (CHCl 3, c 2.00) for =95% ee. 28 [8] a) F. A. Davis, M. C. Weismiller, C. K. Murphy, R. T. Reddy, B. C., Chen, J. rg. Chem. 1992, 57, ; b) F. A. Davis, M. C. Weismiller, J. rg. Chem. 1990, 55, Page 7
9 Spectroscopic data of 28: colorless solid, m.p C; 1 H NMR (400 MHz, CDCl 3 ) δ 8.06 (d, 1 H, J = 7.6 Hz), (m, 1 H), (m, 1 H), (m, 1 H), (m, 3 H), (m, 1 H), (m, 2 H), (m, 1 H), (m, 1 H), 1.61 (s, 3 H), 1.11 (s, 6 H), 0.99 (s, 3 H); 13 C NMR (100 MHz, CDCl 3 ) δ 193.7, 178.1, 165.7, 141.8, 133.8, 130.8, 128.6, 128.3, 127.0, 90.8, 82.7, 54.9, 54.5, 33.2, 30.6, 29.1, 26.8, 21.7, 16.6, 16.4, 9.7; IR (KBr) 2978, 2947, 2883, 1785, 1751, 1697, 1603, 1456, 1315, 1289, 1224, 1171, 1113, 1065, 937, 744 cm 1 ; Anal. Calc d for C 21 H 24 5 : C, 70.77; H, 6.79, Found: C, 70.50; H, 6.91; [ ] 29 D (CHCl 3, c 1.00). CCDC contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via (or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; fax: (+44) ; or deposit@ccdc.cam.ac.uk). Table 2, entry 3 H 18 Spectroscopic data [9] of 18: colorless oil; 1 H NMR (CDCl 3 ) 7.78 (d, 1 H, J = 7.7 Hz), 7.64 (t, 1 H, J = 7.7 Hz), 7.44 (d, 1 H, J = 7.3 Hz), 7.41 (dd, 1 H, J = 7.7, 7.3 Hz), 3.28 (d, 1 H, J = 16.8 Hz), 3.22 (d, 1 H, J = 16.8 Hz), 2.81 (s, 1 H), 1.45 (s, 3 H); 13 C NMR (CDCl 3 ) 208.0, 151.1, 135.8, 133.5, 127.9, 126.7, 124.9, 77.4, 42.2, 25.7; IR (neat) 3434, 3072, 2970, 2925, 1716, 1608, 1468, 1431, 1367, 1300, 1219, 1092, 958, 893, 739 cm 1 ; HPLC (CHIRALCEL D-H, eluent: 2-propanol:hexane = 1:99, flow rate: 1.0 ml/min, 25 C): (S)-18: t 1 = 26.0 min; (R)-18: t 2 = 29.9 min; [ ] 30 D (CHCl 3, c 1.40) for 60% ee; Lit.* [ ] D (CHCl 3, c 1.4) for 78% ee. [9] H. Ziehe, R. Wartchow, H. Butenschoen, Eur. J. rg. Chem. 1999, Page 8
10 29 Spectroscopic data of 29: colorless solid, m.p C; 1 H NMR (400 MHz, CDCl 3 ) δ 7.80 (d, 1 H, J = 7.2 Hz), 7.65 (t, 1 H, J = 7.2 Hz), (m, 2 H), 3.58 (d, 1 H, J = 16.4 Hz), 3.23 (d, 1 H, J = 16.4 Hz), (m, 1 H), (m, 1 H), (m, 1 H), (m, 1 H), 1.53 (s, 3 H), 1.13 (s, 3 H), 1.12 (s, 3 H), 1.01 (s, 3 H); 13 C NMR (100 MHz, CDCl 3 ) δ 201.3, 177.8, 166.2, 148.6, 135.6, 133.6, 127.9, 126.4, 124.6, 90.4, 83.4, 54.8, 54.6, 39.9, 30.5, 29.0, 23.4, 16.7, 16.5, 9.7; IR (KBr) 3033, 2979, 2929, 1790, 1740, 1724, 1608, 1354, 1321, 1269, 1219, 1173, 1092, 1016, 968, 933, 889, 791, 733 cm 1 28 ; Anal. Calc d for C 20 H 22 5 : C, 74.24; H, 5.98, Found: C, 73.96; H, 6.23; [ ] D (CHCl 3, c 0.96). CCDC contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via (or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; fax: (+44) ; or deposit@ccdc.cam.ac.uk). Table 2, entry 4 11 Spectroscopic data of 11: colorless liquid; 1 H NMR (400 MHz, CDCl 3 ) δ 9.84 (s, 1 H), (m, 1 H), (m, 1 H), (m, 4 H), (m, 2 H), 2.25 (s, 3 H); 13 C NMR (100 MHz, CDCl 3 ) δ 201.1, 191.5, 144.6, 139.4, 137.3, 133.8, 133.4, 131.8, 131.0, 130.5, 128.6, 128.3, 128.2, 128.1, 29.4; IR (neat) 3060, 2843, 2750, 1691, 1594, 1250, 827, 762 cm 1. H 19 Page 9
11 Spectroscopic data of 19: colorless solid, m.p C; 1 H NMR (400 MHz, CDCl 3 ) δ 7.98 (dd, 1 H, J = 7.8, 1.5 Hz), 7.95 (d, 1 H, J = 8.3 Hz), (m, 1 H), (m, 1 H), 7.70 (dt, 1 H, J = 1.5, 7.8 Hz), (m, 3 H), 4.03 (bs, 1 H), 1.56 (s, 3 H); 13 C NMR (100 MHz, CDCl 3 ) δ 204.0, 141.5, 137.5, 135.1, 129.5, 128.6, 128.3, 128.1, 127.9, 127.6, 125.6, 124.0, 123.2, 76.9, 32.6; IR (KBr) 3481, 3068, 2977, 2923, 1694, 1601, 1452, 1207, 1077, 757, 732 cm 1 ; Anal. Calc d for C 15 H 12 2 : C, 80.34; H, 5.39; Found: C, 80.57; H, 5.57; HPLC (CHIRALCEL D-H, eluent: 2-propanol:hexane = 1:99, flow rate: 1.0 ml/min, 25 C): (R)-19: t 1 = 21.4 min; (S)-19: t 2 = 30.4 min; [α] 24 D 121 (CHCl 3, c 1.00) for 33% ee. 30 Spectroscopic data of 30: m.p C; 1 H NMR (400 MHz, CDCl 3 ) δ (m, 1 H), (m, 2 H), (m, 1 H), (m, 4 H), (m, 1 H), (m, 2 H), (m, 4 H), 1.29 (s, 3 H), 1.15 (s, 3 H), 1.04 (s, 3 H); 13 C NMR (100 MHz, CDCl 3 ) δ 194.8, 178.6, 166.0, 139.9, 136.6, 135.0, 129.6, 128.6, , , , 127.8, 124.4, 123.8, 123.2, 90.8, 81.7, 55.1, 54.8, 30.3, 28.7, 28.2, 16.7, 16.5, 9.9; IR (KBr) 3062, 2976, 2889, 1778, 1760, 1707, 1604, 1452, 1311, 1263, 1168, 1106, 1018, 764, 737 cm 1 ; Anal. Calc d for C 25 H 24 5 : C, 74.24; H, 5.98, Found: C, 74.08; H, 6.22; [ ] 29 D 126 (CHCl 3, c 0.97). CCDC contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via (or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; fax: (+44) ; or deposit@ccdc.cam.ac.uk). Table 2, entry 5 Page 10
12 Et 12 Spectroscopic data of 12: yellow liquid; 1 H NMR (300 MHz, CDCl 3 ) δ 9.84 (s, 1 H), (m, 1 H), (m, 1 H), (m, 4 H), (m, 2 H), (m, 2 H), 0.96 (t, 3 H, J = 7.2 Hz); 13 C NMR (75 MHz, CDCl 3 ) δ 204.4, 191.5, 144.6, 139.7, 136.9, 133.8, 133.3, 131.7, 130.6, 130.5, 128.2, , , , 34.9, 8.1; IR (neat) 3060, 2978, 2937, 2843, 2750, 1693, 1597, 1250, 1215, 949, 827, 760 cm 1. HEt 20 Spectroscopic data of 20: colorless solid, m.p C; 1 H NMR (400 MHz, CDCl 3 ) δ (m, 2 H), (m, 1 H), (m, 1 H), (m, 1 H), (m, 3 H), 4.03 (bs, 1 H), (m, 2 H), 0.80 (t, 3 H, J = 7.2 Hz); 13 C NMR (100 MHz, CDCl 3 ) δ 203.9, 140.7, 137.5, 134.9, , , 128.4, 128.3, 127.9, 127.0, 126.1, 124.0, 123.1, 80.0, 37.8, 8.2; IR (KBr) 3489, 3068, 2972, 2935, 2875, 1689, 1601, 1452, 1282, 1259, 1201, 1097, 976, 750, 733 cm 1 ; Anal. Calc d for C 16 H 14 2 : C, 80.65; H, 5.92; Found: C, 80.60; H, 6.21; HPLC (CHIRALCEL D-H, eluent: 2- propanol:hexane = 5:95, flow rate: 1.0 ml/min, 25 C): (R)-20: t 1 = 10.1 min; (S)-20: t 2 = 15.5 min; [α] 27 D 265 (CHCl 3, c 1.15) for 90% ee. Et 31 Spectroscopic data of 31: m.p C; 1 H NMR (400 MHz, CDCl 3 ) δ (m, 1 H), (m, 2 H), (m, 1 H), (m, 4 H), (m, 1 H), (m, 1 H), (m, 3 H), (m, 1 H), 1.30 (s, 3 H), 1.15 (s, 3 H), 1.05 (s, 3 H), 0.79 (t, 3 H, J = 7.2 Hz); 13 C NMR (100 MHz, CDCl 3 ) δ 194.6, 178.7, 166.0, 138.8, 136.7, 134.9, 129.3, 128.9, 128.4, 128.3, 127.9, 124.7, 123.8, 123.2, 91.1, Page 11
13 84.8, 77.2, 55.1, 54.8, 31.9, 30.3, 28.7, 16.8, 16.5, 9.9, 7.7; IR (KBr) 2968, 2933, 2877, 1784, 1751, 1689, 1597, 1574, 1450, 1263, 1171, 1103, 1018, 897, 760, 731 cm 1 ; Anal. Calc d for C 26 H 26 5 : C, 74.62; H, 6.26, Found: C, 74.48; H, 6.08; [ ] 23 D 178 (CHCl 3, c 1.06). CCDC contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via (or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; fax: (+44) ; or deposit@ccdc.cam.ac.uk). Table 2, entry 6 i-pr 13 Spectroscopic data of 13: colorless liquid; 1 H NMR (300 MHz, CDCl 3 ) δ 9.86 (s, 1 H), 8.03 (dd, 1 H, J = 7.5, 1.8 Hz), (m, 5 H), (m, 2 H), (m, 1 H), 0.95 (d, 3 H, J = 1.5 Hz), 0.93 (d, 3 H, J = 1.5 Hz); 13 C NMR (75 MHz, CDCl 3 ) δ 208.7, 191.5, 144.4, 139.9, 136.7, 134.0, 133.3, 131.8, 130.6, 130.2, , , 127.9, 127.8, 39.0, 18.9, 18.0; IR (neat) 3060, 2971, 2871, 2751, 1693, 1594, 1467, 1250, 1214, 977, 827, 758 cm 1. Hi-Pr 21 Spectroscopic data of 21: colorless solid, m.p C; 1 H NMR (400 MHz, CDCl 3 ) δ 7.89 (d, 1 H, J = 8.0 Hz), 7.86 (dd, 1 H, J = 8.0, 1.6 Hz), (m, 1 H), (m, 2 H), (m, 3 H), 3.95 (s, 1 H), (m, 1 H), 0.83 (d, 3 H, 6.8 Hz), 0.74 (d, 3 H, 6.8 Hz) ; 13 C NMR (100 MHz, CDCl 3 ) δ 205.1, 139.9, 137.8, 134.8, 129.6, 129.1, , , 127.9, 127.2, 126.8, 124.2, 123.0, 82.1, 38.9, 17.2, 16.6; IR (KBr) 3489, 3068, 2968, 2933, 2873, 1693, 1601, 1452, 1288, 1201, 1109, 1004, 771, 733 cm 1 ; Anal. Calc d for C 17 H 16 2 : C, 80.93; H, 6.39; Found: C, 80.83; H, 6.47; HPLC Page 12
14 (CHIRALCEL D-H, eluent: 2-propanol:hexane = 5:95, flow rate: 1.0 ml/min, 25 C): (R)-21: t 1 = 9.7 min; (S)-21: t 2 = 13.5 min; [α] D (CHCl 3, c 1.04) for 85% ee. i-pr 32 Spectroscopic data of 32: colorless solid, m.p C; 1 H NMR (400 MHz, CDCl 3 ) δ (m, 3 H), (m, 1 H), (m, 4 H), (m, 2 H), (m, 2 H), (m, 1 H), 1.31 (s, 3 H), 1.15 (s, 3 H), 1.05 (s, 3 H), 0.94 (d, 3 H, J = 6.8 Hz), 0.77 (d, 3 H, J = 7.1 Hz); 13 C NMR (100 MHz, CDCl 3 ) δ 194.5, 178.8, 166.0, 137.8, 137.0, 134.7, 130.2, 129.9, 128.8, 128.4, 128.3, 127.4, 125.4, 123.7, 123.1, 91.2, 87.0, 55.2, 54.8, 39.1, 30.4, 28.7, 16.94, 16.91, 16.7, 16.5, 9.9; IR (KBr) 2972, 2937, 2877, 1784, 1751, 1695, 1600, 1452, 1396, 1265, 1171, 1101, 1065, 903, 735 cm 1 ; Anal. Calc d for C 27 H 28 5 : C, 74.98; H, 6.53, Found: C, 75.16; H, 6.76; [ ] 29 D 139 (CHCl 3, c 0.93). CCDC contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via (or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; fax: (+44) ; or deposit@ccdc.cam.ac.uk). Table 2, entry 7 N 14 Spectroscopic data of 14: colorless solid, m.p C; 1 H NMR (400 MHz, CDCl 3 ) δ (d, 1 H, J = 0.7 Hz), (m, 3 H), (m, 2 H), (m, 2 H), 6.87 (dd, 1 H, J = 8.3, 0.7 Hz), 3.51 (s, 3 H), 2.58 (s, 3 H); 13 C NMR (100 MHz, CDCl 3 ) δ 191.1, 189.3, 172.7, 156.8, 156.3, 137.2, 136.3, 132.9, 131.1, 128.6, 128.1, 120.4, 119.8, Page 13
15 119.6, 117.8, , , 55.3, 12.9; IR (KBr) 3062, 3008, 2976, 2943, 2862, 2750, 1693, 1666, 1593, 1473, 1448, 1421, 1389, 1273, 1167, 1074, 903, 700 cm 1 ; Anal. Calc d for C 19 H 15 N 4 : C, 71.02; H, 4.71; N, 4.36, Found: C, 70.98; H, 4.83; N, N H 22 Spectroscopic data of 22: colorless solid, m.p C; 1 H NMR (400 MHz, CDCl 3 ) δ 7.52 (dd, 1 H, J = 7.8, 1.2 Hz), 7.47 (t, 1 H, J = 7.8 Hz), 7.29 (dd, 1 H, J = 7.8, 1.2 Hz), 7.24 (bs, 5 H), 4.56 (brs, 1 H), 4.09 (s, 3 H), 2.50 (s, 3 H); 13 C NMR (100 MHz, CDCl 3 ) δ 198.8, 167.6, 156.8, 154.4, 139.8, 131.6, 131.3, 128.8, 128.5, 125.7, 121.2, 117.8, 117.4, 113.6, 76.5, 56.4, 11.8; IR (KBr) 3424, 2985, 2942, 1695, 1637, 1278, 1248, 1000, 890, 772, 725, 706 cm 1 ; Anal. Calc d for C 19 H 15 N 4 : C, 71.02; H, 4.71; N, 4.36, Found: C, 70.74; H, 4.74; N, 4.12; HPLC (CHIRALPAK AD-H, eluent: 2-propanol:hexane = 24 15:85, flow rate: 1.0 ml/min, 25 C): (R)-22: t 1 = 20.8 min; (S)-22: t 2 = 30.3 min; [α] D 97.9 (CHCl 3, c 1.00) for >99% ee. N Ph 33 The spectroscopic data of 33; colorless solid, m.p. 230 C (decomp.); 1 H NMR (300 MHz, CDCl 3 ) δ 7.66 (d, 1 H, J = 7.6 Hz), 7.50 (t, 1 H, J = 7.6 Hz), (m, 6 H), 4.11 (s, 3 H), (m, 1 H), 2.27 (s, 3 H), (m, 1 H), (m, 1 H), (m, 1 H), 1.21 (s, 3 H), 1.14 (s, 3 H), 0.99 (s, 3 H); 13 C NMR (75 MHz, CDCl 3 ) δ 191.1, 177.8, 166.1, 165.9, 157.3, 154.6, 135.2, 131.5, 131.0, 129.2, 128.9, 126.3, 121.7, 117.4, 117.2, 113.3, 90.4, 80.0, 56.5, 54.8, 54.5, 31.0, 28.9, 16.7, 16.4, 11.5, 9.6; IR (KBr) 2972, 2937, 2841, 1793, 1753, 1699, 1579, 1482, 1311, 1281, 1169, 1109, 1059, 935, 760, 723 cm 1 ; Anal. Calc d for C 29 H 27 N 7 : C, 69.45; H, 5.43; N, 2.79, Found: C, 69.17; H, 5.20; N, 2.57; [α] 22 D 78.8 (CHCl 3, c 1.00). Page 14
16 CCDC contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via (or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; fax: (+44) ; or Table 2, entry 8 N 15 Spectroscopic data of 15: pink solid, m.p. 162 C; 1 H NMR (400 MHz, CDCl 3 ) δ 9.78 (s, 1 H), 7.57 (d, 1 H, J = 8.1 Hz), 7.03 (d, 1 H, J = 8.1 Hz), 6.10 (brs, 2 H), 3.11 (brd, 2 H, J = 3.4 Hz), 2.52 (t, 2 H, J = 6.6 Hz), 2.28 (brs, 2 H); 13 C NMR (100 MHz, CDCl 3 ) δ 191.6, 189.1, 181.1, 153.1, 152.4, 147.6, 129.8, 128.4, 115.6, 109.3, 109.2, 102.6, 37.9, 23.2, 22.1; IR (KBr) 3365, 3091, 2956, 2908, 2729, 1695, 1595, 1506, 1468, 1356, 1265, 1066, 935, 829, 623 cm 1 ; Anal. Calc d for C 15 H 11 N 5 : C, 63.16; H, 3.89; N, 4.91, Found: C, 63.07; H, 4.05; N, N Ac 34 To a suspension of the crude benzoin product 23 (135 mg) in pyridine (1.0 ml) at 0 C was added Ac 2 (0.75 ml) and DMAP (11 mg, mmol). The reaction mixture was warmed to room temperature and then stirred for 1 h. The reaction was quenched by addition of saturated aq NH 4 Cl solution. The products were extracted with CH 2 Cl 2 (20 ml x 3), and the combined organic extracts were washed with brine, dried over Na 2 S 4 and concentrated under reduced pressure. The residue was purified by silicagel preparative thin-layer chromatography (CHCl 3 /H = 97/3) to afford the acetylated product 34 as yellow amorphous solid (72.3 mg, 73 %, 2 steps). The spectroscopic data of 34; 1 H NMR (400 MHz, CDCl 3 ) δ 7.73 (d, 1 H, J = 8.0 Hz), 6.94 (d, 1 H, J = 8.0 Hz), 6.30 (d, 1 H, J = 1.2 Hz), 6.25 (d, 1 H, J = 1.2 Hz), 3.02 (dd, 1 H, J = 18.4, 6.8 Hz), (m, 2 H), (m, 2 H), 1.96 (s, 3 H), (m, 1 H); 13 C NMR (75 Page 15
17 MHz, CDCl 3 ) δ 190.8, 171.6, 169.5, 152.8, 143.8, 126.8, 125.0, 112.9, 109.7, 109.4, 103.3, 77.2, 73.3, 29.3, 22.0, 20.6, 17.5; IR (CHCl 3 ) 3026, 3012, 2964, 2910, 1743, 1689, 1518, 1491, 1454, 1362, 1230, 1124, 1074, 1034, 1011, 972, 829, 779 cm 1 ; Anal. Calc d for C 17 H 13 N 6 : C, 62.39; H, 4.00; N, 4.28, Found: C, 62.14; H, 4.26; N, 3.99; HPLC (CHIRALCEL D-H, eluent: 2-propanol:hexane = 15:85, flow rate: 1.0 ml/min, 25 C): t 1 = 36.7 min; t 2 = 52.4 min; [α] 23 D (CHCl 3, c 1.00) for 99% ee. Scheme 2 24 Spectroscopic data of 24: colorless solid, m.p C; 1 H NMR (300 MHz, CDCl 3 ) δ 10.5 (s, 1 H), 7.87 (dd, 1 H, J = 7.5, 1.8 Hz), (m, 1 H), (m, 5 H), 7.08 (t, 1 H, J = 7.5 Hz), 6.70 (d, 1 H, J = 8.4 Hz), 4.75 (s, 2 H), 3.92 (s, 2 H); 13 C NMR (75 MHz, CDCl 3 ) δ 203.3, 189.2, 159.7, 135.8, 132.6, 129.4, 129.1, 128.9, 127.5, 125.2, 121.8, 112.3, 72.1, 46.5; IR (KBr) 3028, 2898, 2863, 2767, 1722, 1685, 1599, 1483, 1284, 1246, 1061, 769, 704 cm 1.; Anal. Calc d for C 16 H 14 3 : C, 75.57; H, 5.55; Found: C, 75.57; H, 5.57 H 25 Spectroscopic data of 25 [10] : colorless liquid; 1 H NMR (300 MHz, CDCl 3 ) δ 7.89 (dd, 1 H, J = 7.8, 2.1 Hz), (m, 1 H), (m, 7 H), 4.30 (d, 1 H, J = 11.3 Hz), 4.11 (d, 1 H, J = 11.3), 3.58 (bs, 1 H), 3.04 (d, 1 H, J = 13.8 Hz), 2.97 (d, 1 H, J = 13.8 Hz); 13 C NMR (75 MHz, CDCl 3 ) δ 196.0, 161.4, 136.7, 134.3, 130.6, 128.2, 127.6, 127.1, 122.0, 118.4, 118.0, 73.0, 72.2, 40.9; IR (neat) 3475, 3062, 3029, 2920, 2871, 1695, 1608, 1477, 1306, 1217, 1093, 1036, 1018, 764, 700 cm 1 ; Anal. Calc d for C 16 H 14 3 : C, 75.57; H, 5.55; Found: C, 75.50; H, 5.59; HPLC (CHIRALPAK AD-H, eluent: 2- [10] Ref. 8b. Page 16
18 propanol:hexane = 2:98, flow rate: 1.0 ml/min, 25 C): (S)-25: t 1 = 23.8 min; (R)-25: t 2 = 28.8 min; [α] D (CHCl 3, c 3.04) for 88% ee; Lit. [8] [α] D (CHCl 3, c 3.00) for 91% ee. 35 Spectroscopic data of 35: colorless solid, m.p C; 1 H NMR (400 MHz, CDCl 3 ) δ 7.98 (dd, 1 H, J = 8.0, 2.0 Hz), (m, 1 H), (m, 5 H), (m, 1 H), (m, 1 H), 4.98 (d, 1 H, J = 10.8 Hz), 4.14 (d, 1 H, J = 10.8 Hz), 3.25 (d, 1 H, J = 14.4 Hz), 3.13 (d, 1 H, J = 14.4 Hz), (m, 1 H), (m, 2 H), (m, 1 H), 1.13 (s, 6 H), 0.97 (s, 3 H); 13 C NMR (100 MHz, CDCl 3 ) δ 188.9, 177.8, 165.5, 160.6, 136.5, 133.2, 130.9, 128.3, 128.1, 127.5, 122.4, 119.5, 117.9, 90.7, 81.2, 68.0, 54.9, 54.8, 38.9, 30.4, 29.1, 16.7, 16.4, 9.8; IR (KBr) 3070, 3037, 2966, 2935, 2877, 1780, 1761, 1701, 1610, 1475, 1456, 1313, 1259, 1173, 1111, 1049, 1014, 937, 764 cm 1 28 ; Anal. Calc d for C 26 H 26 6 : C, 71.87; H, 6.03, Found: C, 72.17; H, 6.28; [ ] D (CHCl 3, c 1.01). CCDC contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via (or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; fax: (+44) ; or deposit@ccdc.cam.ac.uk). Page 17
Supporting Information. Asymmetric Binary-acid Catalysis with Chiral. Phosphoric Acid and MgF 2 : Catalytic
Supporting Information Asymmetric Binary-acid Catalysis with Chiral Phosphoric Acid and MgF 2 : Catalytic Enantioselective Friedel-Crafts Reactions of β,γ- Unsaturated-α-Ketoesters Jian Lv, Xin Li, Long
Διαβάστε περισσότεραDirect Transformation of Ethylarenes into Primary Aromatic Amides with N-Bromosuccinimide and I 2 -aq NH 3
Supporting Information Direct Transformation of Ethylarenes into Primary Aromatic Amides with N-Bromosuccinimide and I 2 -aq NH 3 Shohei Shimokawa, Yuhsuke Kawagoe, Katsuhiko Moriyama, Hideo Togo* Graduate
Διαβάστε περισσότεραSupporting Information One-Pot Approach to Chiral Chromenes via Enantioselective Organocatalytic Domino Oxa-Michael-Aldol Reaction
Supporting Information ne-pot Approach to Chiral Chromenes via Enantioselective rganocatalytic Domino xa-michael-aldol Reaction Hao Li, Jian Wang, Timiyin E-Nunu, Liansuo Zu, Wei Jiang, Shaohua Wei, *
Διαβάστε περισσότεραA facile and general route to 3-((trifluoromethyl)thio)benzofurans and 3-((trifluoromethyl)thio)benzothiophenes
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2014 A facile and general route to 3-((trifluoromethyl)thio)benzofurans and 3-((trifluoromethyl)thio)benzothiophenes
Διαβάστε περισσότεραSupporting information
Electronic upplementary Material (EI) for New Journal of Chemistry. This journal is The Royal ociety of Chemistry and the Centre National de la Recherche cientifique 7 upporting information Lipase catalyzed,-addition
Διαβάστε περισσότεραHighly enantioselective cascade synthesis of spiropyrazolones. Supporting Information. NMR spectra and HPLC traces
Highly enantioselective cascade synthesis of spiropyrazolones Alex Zea a, Andrea-Nekane R. Alba a, Andrea Mazzanti b, Albert Moyano a and Ramon Rios a,c * Supporting Information NMR spectra and HPLC traces
Διαβάστε περισσότεραHiyama Cross-Coupling of Chloro-, Fluoroand Methoxy- pyridyl trimethylsilanes : Room-temperature Novel Access to Functional Bi(het)aryl
Hiyama Cross-Coupling of Chloro-, Fluoroand Methoxy- pyridyl trimethylsilanes : Room-temperature Novel Access to Functional Bi(het)aryl Philippe Pierrat, Philippe Gros* and Yves Fort Synthèse Organométallique
Διαβάστε περισσότεραMandelamide-Zinc Catalyzed Alkyne Addition to Heteroaromatic Aldehydes
1 Mandelamide-Zinc Catalyzed Alkyne Addition to Heteroaromatic Aldehydes Gonzalo Blay, Isabel Fernández, Alícia Marco-Aleixandre, and José R. Pedro Departament de Química Orgànica, Facultat de Química,
Διαβάστε περισσότεραCopper-catalyzed formal O-H insertion reaction of α-diazo-1,3-dicarb- onyl compounds to carboxylic acids with the assistance of isocyanide
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2014 Copper-catalyzed formal O-H insertion reaction of α-diazo-1,3-dicarb- onyl compounds to carboxylic
Διαβάστε περισσότεραRoom Temperature Highly Diastereoselective Zn-Mediated. Allylation of Chiral N-tert-Butanesulfinyl Imines: Remarkable Reaction Condition Controlled
Supporting Information for: Room Temperature Highly Diastereoselective Zn-Mediated Allylation of Chiral N-tert-Butanesulfinyl Imines: Remarkable Reaction Condition Controlled Stereoselectivity Reversal
Διαβάστε περισσότεραSupporting Information
Supporting Information Lewis acid catalyzed ring-opening reactions of methylenecyclopropanes with diphenylphosphine oxide in the presence of sulfur or selenium Min Shi,* Min Jiang and Le-Ping Liu State
Διαβάστε περισσότεραFacile construction of the functionalized 4H-chromene via tandem. benzylation and cyclization. Jinmin Fan and Zhiyong Wang*
Facile construction of the functionalized 4H-chromene via tandem benzylation and cyclization Jinmin Fan and Zhiyong Wang* Hefei National Laboratory for Physical Science at Microscale, Joint- Lab of Green
Διαβάστε περισσότεραSupporting Information
Supporting Information Montmorillonite KSF-Catalyzed One-pot, Three-component, Aza-Diels- Alder Reactions of Methylenecyclopropanes With Arylaldehydes and Aromatic Amines Li-Xiong Shao and Min Shi* General
Διαβάστε περισσότεραSupporting Information. Experimental section
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2014 Supporting Information Experimental section General. Proton nuclear magnetic resonance ( 1
Διαβάστε περισσότεραSupporting Information
Supporting Information Siloxy(trialkoxy)ethene Undergoes Regioselective [2+2] Cycloaddition to Ynones and Ynoates en route to Functionalized Cyclobutenediones Shin Iwata, Toshiyuki Hamura, and Keisuke
Διαβάστε περισσότεραDirect Palladium-Catalyzed Arylations of Aryl Bromides. with 2/9-Substituted Pyrimido[5,4-b]indolizines
Direct Palladium-Catalyzed Arylations of Aryl Bromides with 2/9-Substituted Pyrimido[5,4-b]indolizines Min Jiang, Ting Li, Linghua Meng, Chunhao Yang,* Yuyuan Xie*, and Jian Ding State Key Laboratory of
Διαβάστε περισσότεραElectronic Supplementary Information
Electronic Supplementary Information Unprecedented Carbon-Carbon Bond Cleavage in Nucleophilic Aziridine Ring Opening Reaction, Efficient Ring Transformation of Aziridines to Imidazolidin-4-ones Jin-Yuan
Διαβάστε περισσότεραLewis Acid Catalyzed Propargylation of Arenes with O-Propargyl Trichloroacetimidate: Synthesis of 1,3-Diarylpropynes
Supporting Information for Lewis Acid Catalyzed Propargylation of Arenes with O-Propargyl Trichloroacetimidate: Synthesis of 1,3-Diarylpropynes Changkun Li and Jianbo Wang* Beijing National Laboratory
Διαβάστε περισσότεραSupporting Information. Copyright Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2006
Supporting Information Copyright Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 2006 1 A Facile Way to Synthesize 2H-Chromenes: Reconsideration of the Reaction Mechanism between Salicylic Aldehyde and
Διαβάστε περισσότεραand Selective Allylic Reduction of Allylic Alcohols and Their Derivatives with Benzyl Alcohol
FeCl 3 6H 2 O-Catalyzed Disproportionation of Allylic Alcohols and Selective Allylic Reduction of Allylic Alcohols and Their Derivatives with Benzyl Alcohol Jialiang Wang, Wen Huang, Zhengxing Zhang, Xu
Διαβάστε περισσότεραSupporting Information
Supporting Information for AgOTf-catalyzed one-pot reactions of 2-alkynylbenzaldoximes with α,β-unsaturated carbonyl compounds Qiuping Ding 1, Dan Wang 1, Puying Luo* 2, Meiling Liu 1, Shouzhi Pu* 3 and
Διαβάστε περισσότεραSupporting Information
Supporting Information Ceric Ammonium Nitrate (CAN) catalyzed efficient one-pot three component aza-diels-alder reactions for a facile synthesis of tetrahydropyranoquinoline derivatives Ravinder Goud Puligoundla
Διαβάστε περισσότεραSupporting Information. Experimental section
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2014 Supporting Information Experimental section General. Anhydrous solvents were transferred by
Διαβάστε περισσότεραVilsmeier Haack reagent-promoted formyloxylation of α-chloro-narylacetamides
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 205 Vilsmeier aack reagent-promoted formyloxylation of α-chloro-arylacetamides by formamide Jiann-Jyh
Διαβάστε περισσότεραDivergent synthesis of various iminocyclitols from D-ribose
Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 205 Divergent synthesis of various iminocyclitols from D-ribose Ramu Petakamsetty,
Διαβάστε περισσότεραSite-Selective Suzuki-Miyaura Cross-Coupling Reactions of 2,3,4,5-Tetrabromofuran
1 Site-Selective Suzuki-Miyaura Cross-Coupling Reactions of 2,3,4,5-Tetrabromofuran Munawar Hussain, a Rasheed Ahmad Khera, a Nguyen Thai Hung, a Peter Langer* a,b a Institut für Chemie, Universität Rostock,
Διαβάστε περισσότεραElectronic Supplementary Information (ESI)
Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry Electronic Supplementary Information (ESI) For Iron-Catalysed xidative Amidation of Alcohols with Amines Silvia Gaspa, a Andrea
Διαβάστε περισσότεραSupporting Information
Supporting Information for Lewis acid-catalyzed redox-neutral amination of 2-(3-pyrroline-1-yl)benzaldehydes via intramolecular [1,5]-hydride shift/isomerization reaction Chun-Huan Jiang, Xiantao Lei,
Διαβάστε περισσότεραSupporting information
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2014 Supporting information Copper-catalysed intramolecular O-arylation: a simple
Διαβάστε περισσότεραChiral Brønsted Acid Catalyzed Enantioselective Intermolecular Allylic Aminations. Minyang Zhuang and Haifeng Du*
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2014 Chiral Brønsted Acid Catalyzed Enantioselective Intermolecular Allylic
Διαβάστε περισσότεραSupporting Information
Supporting Information Wiley-VC 007 9 Weinheim, Germany ew ear Infrared Dyes and Fluorophores Based on Diketopyrrolopyrroles Dipl.-Chem. Georg M. Fischer, Dipl.-Chem. Andreas P. Ehlers, Prof. Dr. Andreas
Διαβάστε περισσότεραSupporting Information
Supporting Information Copper/Silver Cocatalyzed Oxidative Coupling of Vinylarenes with ICH 2 CF 3 or ICH 2 CHF 2 Leading to β-cf 3 /CHF 2 -Substituted Ketones Niannian Yi, Hao Zhang, Chonghui Xu, Wei
Διαβάστε περισσότεραSupporting Information
S1 Supporting Information Synthesis of 2-Arylated Hydroxytyrosol Derivatives via Suzuki-Myaura Cross-Coupling Roberta Bernini, a Sandro Cacchi, b* Giancarlo Fabrizi, b* Eleonora Filisti b a Dipartimento
Διαβάστε περισσότεραThe Free Internet Journal for Organic Chemistry
The Free Internet Journal for Organic Chemistry Paper Archive for Organic Chemistry Arkivoc 2018, part iii, S1-S6 Synthesis of dihydropyranones and dihydropyrano[2,3- d][1,3]dioxine-diones by cyclization
Διαβάστε περισσότεραTributylphosphine-Catalyzed Cycloaddition of Aziridines with Carbon Disulfide and Isothiocyanate
upporting Information Tributylphosphine-Catalyzed Cycloaddition of Aziridines with Carbon Disulfide and Isothiocyanate Jing-Yu Wu, Zhi-Bin Luo, Li-Xin Dai and Xue-Long Hou* a tate Key Laboratory of Organometallic
Διαβάστε περισσότεραChiral Phosphoric Acid Catalyzed Asymmetric Synthesis of 2-Substituted 2,3-Dihydro-4-Quinolones by Protecting Group-Free Approach
Chiral Phosphoric Acid Catalyzed Asymmetric Synthesis of 2-Substituted 2,3-Dihydro-4-Quinolones by Protecting Group-Free Approach Kodai Saito, Yuka Moriya, and Takahiko Akiyama* Department of Chemistry,
Διαβάστε περισσότεραSupporting Information. Synthesis and biological evaluation of 2,3-Bis(het)aryl-4-azaindoles Derivatives as protein kinases inhibitors
Supporting Information Synthesis and biological evaluation of 2,3-Bis(het)aryl-4-azaindoles Derivatives as protein kinases inhibitors Frédéric Pin, a Frédéric Buron, a Fabienne Saab, a Lionel Colliandre,
Διαβάστε περισσότεραRegioselectivity in the Stille coupling reactions of 3,5- dibromo-2-pyrone.
Regioselectivity in the Stille coupling reactions of 3,5- dibromo-2-pyrone. Won-Suk Kim, Hyung-Jin Kim and Cheon-Gyu Cho Department of Chemistry, Hanyang University, Seoul 133-791, Korea Experimental Section
Διαβάστε περισσότεραSupporting Information
Supporting Information Wiley-VCH 2008 69451 Weinheim, Germany Diphenylprolinol Silyl Ether as a Catalyst in an Enantioselective, Catalytic, Formal Aza [3+3] Cycloaddition Reaction for the Formation of
Διαβάστε περισσότεραDiastereo- and Enantioselective Propargylation of Benzofuranones. Catalyzed by Pybox-Copper Complex
Diastereo- and Enantioselective Propargylation of Benzofuranones Catalyzed by Pybox-Copper Complex Long Zhao, Guanxin Huang, Beibei Guo, Lijun Xu, Jie Chen, Weiguo Cao, Gang Zhao, *, Xiaoyu Wu *, Department
Διαβάστε περισσότεραEnantioselective Organocatalytic Michael Addition of Isorhodanines. to α, β-unsaturated Aldehydes
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2016 Enantioselective Organocatalytic Michael Addition of Isorhodanines to α,
Διαβάστε περισσότεραFirst DMAP-mediated direct conversion of Morita Baylis. Hillman alcohols into γ-ketoallylphosphonates: Synthesis of
Supporting Information File 1 for First DMAP-mediated direct conversion of Morita Baylis Hillman alcohols into γ-ketoallylphosphonates: Synthesis of γ-aminoallylphosphonates Marwa Ayadi 1,2, Haitham Elleuch
Διαβάστε περισσότεραOxyhalogenation of thiols and disulfides into sulfonyl chlorides/ bromides in water using oxone-kx(x= Cl or Br)
Electronic Supplementary Material (ESI) for Green Chemistry. This journal is The Royal Society of Chemistry 2014 Oxyhalogenation of thiols and disulfides into sulfonyl chlorides/ bromides in water using
Διαβάστε περισσότεραRh(III)-Catalyzed C-H Amidation with N-hydroxycarbamates: A. new Entry to N-Carbamate Protected Arylamines
Rh(III)-Catalyzed C-H Amidation with N-hydroxycarbamates: A new Entry to N-Carbamate Protected Arylamines Bing Zhou,* Juanjuan Du, Yaxi Yang,* Huijin Feng, Yuanchao Li Shanghai Institute of Materia Medica,
Διαβάστε περισσότεραSupplementary information
Electronic Supplementary Material (ESI) for MedChemComm. This journal is The Royal Society of Chemistry 2015 Supplementary information Synthesis of carboxyimidamide-substituted benzo[c][1,2,5]oxadiazoles
Διαβάστε περισσότεραPhosphorus Oxychloride as an Efficient Coupling Reagent for the Synthesis of Ester, Amide and Peptide under Mild Conditions
Supplementary Information for Phosphorus xychloride as an Efficient Coupling Reagent for the Synthesis of Ester, Amide and Peptide under Mild Conditions u Chen,* a,b Xunfu Xu, a Liu Liu, a Guo Tang,* a
Διαβάστε περισσότεραSupplement: Intramolecular N to N acyl migration in conformationally mobile 1 -acyl-1- systems promoted by debenzylation conditions (HCOONH 4
Cent. Eur. J. Chem. 9(5) 2011 S164-S175 DI: 10.2478/s11532-011-0082-y Central European Journal of Chemistry Supplement: Intramolecular to acyl migration in conformationally mobile 1 -acyl-1- benzyl-3,4
Διαβάστε περισσότεραSupporting Information
Electronic Supplementary Material (ESI) for rganic Chemistry Frontiers. This journal is the Partner rganisations 2018 Palladium-catalyzed direct approach to α-cf 3 aryl ketones from arylboronic acids Bo
Διαβάστε περισσότερα9-amino-(9-deoxy)cinchona alkaloids-derived novel chiral phase-transfer catalysts
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2014 9-amino-(9-deoxy)cinchona alkaloids-derived novel chiral phase-transfer
Διαβάστε περισσότεραSupporting Information for Iron-catalyzed decarboxylative alkenylation of cycloalkanes with arylvinylic carboxylic acids via a radical process
Supporting Information for Iron-catalyzed decarboxylative alkenylation of cycloalkanes with arylvinylic carboxylic acids via a radical process Jincan Zhao 1, Hong Fang 1, Jianlin Han* 1,2 and Yi Pan* 1
Διαβάστε περισσότεραFluorinative Ring-opening of Cyclopropanes by Hypervalent Iodine Reagents. An Efficient Method for 1,3- Oxyfluorination and 1,3-Difluorination
Electronic Supplementary Material (ESI) for Chemical Science. This journal is The Royal Society of Chemistry 2016 Supporting Information Fluorinative Ring-opening of Cyclopropanes by Hypervalent Iodine
Διαβάστε περισσότεραSupporting Information
Supporting Information Lewis Acid Mediated [2,3]-Sigmatropic Rearrangement of Allylic α-amino Amides. Jan Blid, Peter Brandt, Peter Somfai*, Department of Chemistry, rganic Chemistry, Royal Institute of
Διαβάστε περισσότεραSupporting Information
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2015 Synthesis of 3-omosubstituted Pyrroles via Palladium- Catalyzed Intermolecular Oxidative Cyclization
Διαβάστε περισσότεραFirst Total Synthesis of Antimitotic Compound, (+)-Phomopsidin
First Total Synthesis of Antimitotic Compound, (+)-Phomopsidin Takahiro Suzuki, a Kenji Usui, a Yoshiharu Miyake, a Michio Namikoshi, b and Masahisa Nakada a, * a Department of Chemistry, School of Science
Διαβάστε περισσότεραAminofluorination of Fluorinated Alkenes
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2018 Synthesis of ɑ CF 3 and ɑ CF 2 H Amines via Aminofluorination of Fluorinated Alkenes Ling Yang,
Διαβάστε περισσότεραSupporting Information. Table of Contents. II. Experimental procedures. II. Copies of 1H and 13C NMR spectra for all compounds
Electronic upplementary Material (EI) for rganic & Biomolecular Chemistry. This journal is The Royal ociety of Chemistry 2017 Laboratoire de Méthodologie et ynthèse de Produit aturels. Université du Québec
Διαβάστε περισσότεραCopper-Catalyzed Oxidative Dehydrogenative N-N Bond. Formation for the Synthesis of N,N -Diarylindazol-3-ones
Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers. This journal is the Partner Organisations 2016 Supporting information Copper-Catalyzed Oxidative Dehydrogenative - Bond Formation
Διαβάστε περισσότεραSupporting Information For: Rhodium-Catalyzed Hydrofunctionalization: Enantioselective Coupling of Indolines and 1,3-Dienes
Supporting Information For: Rhodium-Catalyzed Hydrofunctionalization: Enantioselective Coupling of Indolines and 1,3-Dienes Xiao-Hui Yang and Vy M. Dong* dongv@uci.edu Department of Chemistry, University
Διαβάστε περισσότεραElectronic Supplementary Information
Electronic Supplementary Information NbCl 3 -catalyzed [2+2+2] intermolecular cycloaddition of alkynes and alkenes to 1,3-cyclohexadiene derivatives Yasushi Obora,* Keisuke Takeshita and Yasutaka Ishii*
Διαβάστε περισσότεραProtease-catalysed Direct Asymmetric Mannich Reaction in Organic Solvent
Supplementary information for the paper Protease-catalysed Direct Asymmetric Mannich Reaction in Organic Solvent Yang Xue, Ling-Po Li, Yan-Hong He * & Zhi Guan * School of Chemistry and Chemical Engineering,
Διαβάστε περισσότεραSupporting Information for
Supporting Information for An atom-economic route to densely functionalized thiophenes via base-catalyzed rearrangement of 5-propargyl-2H-thiopyran-4(3H)-ones Chunlin Tang a, Jian Qin b, Xingqi Li *a a
Διαβάστε περισσότεραESI for. A simple and efficient protocol for the palladium-catalyzed. ligand-free Suzuki reaction at room temperature in aqueous DMF.
ESI for A simple and efficient protocol for the palladium-catalyzed ligand-free Suzuki reaction at room temperature in aqueous DMF Chun Liu,* Qijian i, Fanying Bao and Jieshan Qiu State Key Laboratory
Διαβάστε περισσότεραCopper-Catalyzed Oxidative Coupling of Acids with Alkanes Involving Dehydrogenation: Facile Access to Allylic Esters and Alkylalkenes
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2014 Supplementary information Copper-Catalyzed xidative Coupling of Acids with Alkanes Involving Dehydrogenation:
Διαβάστε περισσότεραRhodium-Catalyzed Oxidative Decarbonylative Heck-type Coupling of Aromatic Aldehydes with Terminal Alkenes
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2015 Electronic Supplementary Information Rhodium-Catalyzed Oxidative Decarbonylative Heck-type
Διαβάστε περισσότεραSupporting Information
Supporting Information Wiley-VCH 2007 69451 Weinheim, Germany Supporting Information for Catalytic Enantioselective Conjugate Reduction of β,β- Disubstituted α,β-unsaturated sulfones Tomás Llamas, Ramón
Διαβάστε περισσότεραOne-pot β-substitution of enones with alkyl groups to β-alkyl enones
Electronic Supplementary Information ne-pot β-substitution of enones with alkyl groups to β-alkyl enones Jun-ichi Matsuo* and Yayoi Aizawa Center for Basic Research, The Kitasato Institute, 1-15-1-S105,
Διαβάστε περισσότεραSupporting Information
Supporting Information An Approach to 3,6-Disubstituted 2,5-Dioxybenzoquinones via Two Sequential Suzuki Couplings. Three-step Synthesis of Leucomelone Xianwen Gan, Wei Jiang, Wei Wang,,,* Lihong Hu,,*
Διαβάστε περισσότεραSupplementary Information for
Supplementary Information for Organocatalytic Asymmetric Intramolecular [3+2] Cycloaddition: A Straightforward Approach to Access Multiply Substituted Hexahydrochromeno[4,3-b]pyrrolidine Derivatives in
Διαβάστε περισσότεραSupporting Information
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2017 Modular Synthesis of Propargylamine Modified Cyclodextrins by a Gold(III)-catalyzed Three Component
Διαβάστε περισσότεραSupporting Information
Electronic upplementary Material (EI) for Green Chemistry. This journal is The Royal ociety of Chemistry 204 upporting Information ynthesis of sulfonamides via I 2 -mediated reaction of sodium sulfinates
Διαβάστε περισσότεραPd Catalyzed Carbonylation for the Construction of Tertiary and
Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2014 Pd Catalyzed Carbonylation for the Construction of Tertiary and Quaternary
Διαβάστε περισσότεραSupplementary Data. Engineering, Nanjing University, Nanjing , P. R. China;
Supplementary Data Synthesis, Chemo-selective Properties of Substituted 9-Aryl-9H-fluorenes from Triarylcarbinols and Enantiomerical Kinetics of Chiral 9-Methoxy-11-(naphthalen-1-yl)-11H-benzo[a]fluorene
Διαβάστε περισσότεραAluminium-mediated Aromatic C F Bond Activation: Regioswitchable Construction of Benzene-fused Triphenylene. Frameworks
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2016 Aluminium-mediated Aromatic C Bond Activation: Regioswitchable Construction of Benzene-fused Triphenylene
Διαβάστε περισσότεραSupporting Information for
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2015 Supporting Information for Quinine-Catalyzed Highly Enantioselective Cycloannulation
Διαβάστε περισσότεραSUPPLEMENTARY INFORMATION
DOI: 10.1038/NCHEM.1998 An organic thiyl radical catalyst for enantioselective cyclization Takuya Hashimoto, Yu Kawamata and Keiji Maruoka Department of Chemistry, Graduate School of Science, Kyoto University,
Διαβάστε περισσότεραSupporting Information
Supporting Information Selective Synthesis of xygen-containing Heterocycles via Tandem Reactions of 1,2-Allenic Ketones with Ethyl 4-Chloroacetoacetate Qiang Wang, a, b Zhouqing Xu b and Xuesen Fan a *
Διαβάστε περισσότεραThe N,S-Bidentate Ligand Assisted Pd-Catalyzed C(sp 2 )-H. Carbonylation using Langlois Reagent as CO Source. Supporting Information.
Electronic upplementary Material (EI) for rganic & Biomolecular Chemistry. This journal is The Royal ociety of Chemistry 2018 The,-Bidentate Ligand Assisted Pd-Catalyzed C(sp 2 )-H Carbonylation using
Διαβάστε περισσότεραSupporting Information for. Palladium-catalyzed Addition Reaction of Aroyl/Heteroaroyl Acid Anhydrides to Norbornenes
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2014 Supporting Information for Palladium-catalyzed Addition Reaction of Aroyl/Heteroaroyl Acid Anhydrides
Διαβάστε περισσότεραEco-friendly synthesis of diverse and valuable 2-pyridones by catalyst- and solvent-free thermal multicomponent domino reaction
Electronic Supplementary Material (ESI) for Green Chemistry. This journal is The Royal Society of Chemistry 2015 SUPPRTIG IFRMATI Eco-friendly synthesis of diverse and valuable 2-pyridones by catalyst-
Διαβάστε περισσότεραAsymmetric Synthesis of New Chiral β-amino Acid Derivatives by Mannich-type Reactions of Chiral N- Sulfinyl Imidates with N-Tosyl Aldimines
Asymmetric Synthesis of New Chiral β-amino Acid Derivatives by Mannich-type Reactions of Chiral N- Sulfinyl Imidates with N-yl Aldimines Filip Colpaert, Sven Mangelinckx, and Norbert De Kimpe Department
Διαβάστε περισσότεραFerric(III) Chloride Catalyzed Halogenation Reaction of Alcohols and Carboxylic Acids using - Dichlorodiphenylmethane
Supporting Information Ferric(III) Chloride Catalyzed Halogenation Reaction of Alcohols and Carboxylic Acids using - Dichlorodiphenylmethane Chang-Hee Lee,, Soo-Min Lee,, Byul-Hana Min, Dong-Su Kim, Chul-Ho
Διαβάστε περισσότεραSupporting Information. Synthesis and biological evaluation of nojirimycin- and
Supporting Information for Synthesis and biological evaluation of nojirimycin- and pyrrolidine-based trehalase inhibitors Davide Bini 1, Francesca Cardona 2, Matilde Forcella 1, Camilla Parmeggiani 2,3,
Διαβάστε περισσότεραSupporting Information
Supporting Information Copyright Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 2010 A Highly Effective Bis(sulfonamide) Diamine Ligand: A Unique Chiral Skeleton for the Enantioselective Cu-Catalyzed
Διαβάστε περισσότεραCopper-Catalyzed Direct Acyloxylation of C(sp 2 ) H Bonds. in Aromatic Amides
Supporting Information for Copper-Catalyzed Direct Acyloxylation of C(sp 2 ) H Bonds in Aromatic Amides Feifan Wang, Qiyan Hu, Chao Shu, Zhiyang Lin, Dewen Min, Tianchao Shi and Wu Zhang* Key Laboratory
Διαβάστε περισσότεραFree Radical Initiated Coupling Reaction of Alcohols and. Alkynes: not C-O but C-C Bond Formation. Context. General information 2. Typical procedure 2
Free Radical Initiated Coupling Reaction of Alcohols and Alkynes: not C-O but C-C Bond Formation Zhongquan Liu,* Liang Sun, Jianguo Wang, Jie Han, Yankai Zhao, Bo Zhou Institute of Organic Chemistry, Gannan
Διαβάστε περισσότεραCopper-mediated radical cross-coupling reaction of 2,2-dichloro-1,1,1-trifluoroethane (HCFC-123) with phenols or thiophenols. Support Information
Copper-mediated radical cross-coupling reaction of 2,2-dichloro-1,1,1-trifluoroethane (HCFC-123) with phenols or thiophenols Dr. Xiao un Tang and Prof. Qing un Chen* Key Laboratory of Organofluorine Chemistry,
Διαβάστε περισσότεραmulticomponent synthesis of 5-amino-4-
Supporting Informartion for Molecular iodine-catalyzed one-pot multicomponent synthesis of 5-amino-4- (arylselanyl)-1h-pyrazoles Camila S. Pires 1, Daniela H. de Oliveira 1, Maria R. B. Pontel 1, Jean
Διαβάστε περισσότεραConstruction of 1,3-Dithio-Substituted Tetralins by [1,5]-Alkylthio Group Transfer Mediated Skeletal Rearrangement
Construction of 1,3-Dithio-Substituted Tetralins by [1,5]-Alkylthio Group Transfer Mediated Skeletal Rearrangement Naoya Hisano, Yuto Kamei, Yaoki Kansaku, and Keiji Mori * Masahiro Yamanaka, Department
Διαβάστε περισσότεραSupplementary Information. Bio-catalytic asymmetric Mannich reaction of ketimines using. wheat germ lipase
Electronic Supplementary Material (ESI) for Catalysis Science & Technology. This journal is The Royal Society of Chemistry 2016 Supplementary Information Bio-catalytic asymmetric Mannich reaction of ketimines
Διαβάστε περισσότεραMetal-free Oxidative Coupling of Amines with Sodium Sulfinates: A Mild Access to Sulfonamides
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2014 Supporting information for Metal-free Oxidative Coupling of Amines with Sodium Sulfinates:
Διαβάστε περισσότεραSupporting Materials
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2016 Carbonylative Coupling of Aryl Tosylates/triflates with Arylboronic Acids under CO Atmosphere
Διαβάστε περισσότεραPeptidomimetics as Protein Arginine Deiminase 4 (PAD4) Inhibitors
Peptidomimetics as Protein Arginine Deiminase 4 (PAD4) Inhibitors Andrea Trabocchi a, icolino Pala b, Ilga Krimmelbein c, Gloria Menchi a, Antonio Guarna a, Mario Sechi b, Tobias Dreker c, Andrea Scozzafava
Διαβάστε περισσότεραSupporting Information
Supporting Information Gold-catalyzed Cycloisomerization of 1,6-Diyne-4-en-3-ols to form Naphthyl Ketone Derivatives. Jian-Jou Lian and Rai-Shung Liu* Department of Chemistry, National Tsing-Hua University,
Διαβάστε περισσότεραKishore Natte, Jianbin Chen, Helfried Neumann, Matthias Beller, and Xiao-Feng Wu*
Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 204 Kishore Natte, Jianbin Chen, Helfried Neumann, Matthias Beller, and Xiao-Feng
Διαβάστε περισσότεραSUPPORTING INFORMATION. Transition Metal-Free Arylations of In-Situ Generated Sulfenates with Diaryliodonium Salts
S1 SUPPORTING INFORMATION Transition Metal-Free Arylations of In-Situ Generated Sulfenates with Diaryliodonium Salts Hao Yu, Zhen Li, and Carsten Bolm* Institute of Organic Chemistry, RWTH Aachen University
Διαβάστε περισσότεραSupporting Information
Supporting Information Transition-metal-free Ring Expansion Reactions of Indene-1,3-dione: Synthesis of Functionalized Benzoannulated Seven-Membered Ring Compounds Qiyi Yao, Lingkai Kong, Mengdan Wang,
Διαβάστε περισσότεραSupporting Information. for. Highly Selective Hydroiodation of Alkynes Using. Iodine-Hydrophosphine Binary System
Supporting Information for Highly Selective Hydroiodation of Alkynes Using Iodine-Hydrophosphine Binary System Shin-ichi Kawaguchi and Akiya Ogawa * Department of Applied Chemistry, Graduate School of
Διαβάστε περισσότεραSupporting Information
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2014 Supporting Information A Convenient and Efficient Synthesis of Glycals by Zinc Nanoparticles
Διαβάστε περισσότεραExperimental procedure
Supporting Information for Direct electrophilic N-trifluoromethylthiolation of amines with trifluoromethanesulfenamide Sébastien Alazet 1,2, Kevin Ollivier 1 and Thierry Billard* 1,2 Address: 1 Institute
Διαβάστε περισσότεραAsymmetric Allylic Alkylation of Ketone Enolates: An Asymmetric Claisen Surrogate.
Asymmetric Allylic Alkylation of Ketone Enolates: An Asymmetric Claisen Surrogate. Erin C. Burger and Jon A. Tunge* Department of Chemistry, University of Kansas, Lawrence, KS 0 Supporting Information
Διαβάστε περισσότερα