Supplementary Information for
|
|
|
- Ἀληκτώ Αλεβίζος
- 6 χρόνια πριν
- Προβολές:
Transcript
1 Supplementary Information for Organocatalytic Asymmetric Intramolecular [3+2] Cycloaddition: A Straightforward Approach to Access Multiply Substituted Hexahydrochromeno[4,3-b]pyrrolidine Derivatives in High Optical Purity Nan Li, a,b Jin Song, c Xi-Feng Tu, c Bin Liu, c Xiao-Hua Chen, c and Liu-Zhu Gong a,c * a. Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, , China b. Graduate School of Chinese Academy of Sciences, Beijing, , China c. Hefei National Laboratory for Physical Sciences at the Microscale and Department of Chemistry, University of Science and Technology of China, Hefei, , China. gonglz@ustc.edu.cn General data: NMR spectra were recorded on a Brucker-400 MHz spectrometer. Optical rotations were measured on a Perkin-Elmer 241 Polarimeter at = 589 nm (sodium D line). HRMS (Micromass GCT-MS) spectra were recorded on P-SIMS-Gly of Bruker Daltonics Inc. Infrared spectra were recorded on a Nicolet MX-1E FT-IR spectromter. Melting points were determined on a digital melting point apparatus and temperatures were uncorrected. HPLC analysis was performed on Waters-Breeze (2487 Dual Absorbance Detector and 1525 Binary HPLC Pump). Chiralpak AS, AD, OD and IA columns were purchased from Daicel Chemical Industries, Ltd. Toluene was refluxed with sodium and benzophenone and distilled prior to use. Petroleum ether and ethyl acetate for column chromatography were distilled before use. The relative and absolute configuration of 3d was assigned by the X-ray analysis. Materials: All starting materials were purchased from Acros, Alfa Aesar, Aldrich and used directly The preparation of chiral phosphoric acid 4g: Chiral catalyst was prepared on the base of the literature procedures. 1 General Procedure for the synthesis of aldehyde substrates. Different substituted 2-hydroxybenzaldehydes, (E)-ethyl 4-bromobut-2-enoate or (E)-methyl 4-bromobut-2-enoate and K 2 CO 3 were dissolved in DMF. After the reaction system was heated at 70 o C under argon for 4 hours, it was filtrated and then added H 2 O. The mixture was extracted with EtOAc (20 ml X 3). The combined organic phases were washed with H 2 O and saturated NaCl, and dried over anhydrous S1
2 Na 2 SO 4. After removal of solvent under reduced pressure, the residue was purified through flash column chromatography on a silica gel (eluent: petroleum ether: ethyl acetate) to give the pure products. (E)-Ethyl 4-(2-formylphenoxy)but-2-enoate (1a). 67% yield (Flash column chromatography eluent, petroleum ether / ethyl acetate = 80: 1 to 10: 1); yellow solid, mp: o C; 1 H-NMR (CDCl 3, 400 MHz) δ (ppm): 1.31 (t, J= 7.1 Hz, 3H), 4.20 (q, J= 7.1 Hz, 2H), 4.82 (q, J= 2.0 Hz, 2H), (m, 1H), 6.94 (d, J= 8.4 Hz, 1H), (m, 2H), (m, 1H), 7.87 (dd, J 1 = 1.8 Hz, J 2 = 15.3 Hz, 1H), (s, 1H); 13 C NMR (CDCl 3, 101 MHz) δ (ppm): 14.59, 61.12, 67.29, , , , , , , ; IR (KBr): γ 3399, 2986, 2874, 1714, 1688, 1663, 1600, 1479, 1438, 1379, 1305, 1249, 1183, 1075, 1041, 969, 946, 850, 769, 682, 661, 614 cm -1 ; HRMS (Micromass GCT-MS EI) exact mass calcd for (C 13 H 14 O 4 ) + requires m/z , found m/z (E)-Ethyl 4-(4-chloro-2-formylphenoxy)but-2-enoate (1b). 67% yield (Flash column chromatography eluent, petroleum ether / ethyl acetate / CH 2 Cl 2 = 30: 1: 1); white solid, mp: o C; 1 H-NMR (CDCl 3, 400 MHz) δ (ppm): 1.26 (t, J= 7.1 Hz, 3H), 4.16 (q, J= 7.1 Hz, 2H), 4.77 (q, J= 2.0 Hz, 2H), (m, 1H), 6.85 (d, J= 8.9 Hz, 1H), (m, 1H), 7.44 (dd, J 1 = 2.7 Hz, J 2 = 17.7 Hz, 1H), (s, 1H); 13 C NMR (CDCl 3, 101 MHz) δ (ppm): 14.58, 61.19, 67.68, , , , , , , , , , ; IR (KBr): γ 3408, 2986, 2908, 2869, 1719, 1684, 1594, 1482, 1437, 1307, 1272, 1183, 1127, 1040, 975, 844, 680 cm -1 ; HRMS (Micromass GCT-MS EI) exact mass calcd for (C 13 H 13 ClO 4 ) + requires m/z , found m/z (E)-Ethyl 4-(2-formyl-4-methoxyphenoxy)but-2-enoate (1c). 72% yield (Flash column chromatography eluent, petroleum ether / ethyl acetate= 70: 1 to 40: 1); yellow solid, mp: o C; 1 H-NMR (CDCl 3, 400 MHz) δ (ppm): 1.30 (t, J= 7.1 Hz, 3H), 3.80 (s, 3H), 4.20 (q, J= 7.1 Hz, 2H), 4.78 (q, J= 2.0 Hz, 2H), 6.19 (d, J= 15.7 Hz, 1H), 6.90 (d, J= 9.0 Hz, 1H), (m, 2H), 7.35 (d, J= 3.0 Hz, 1H), (s, 1H); 13 C NMR (CDCl 3, 101 MHz) δ (ppm): 14.22, 55.84, 60.71, 67.64, , , , , , , , , , ; IR (KBr): γ 3438, 2981, 2874, 1720, 1677, 1616, 1496, 1450, 1285, 1214, 1184, 1087, 1035, 942, 873, 817, 728, 647 cm -1 ; HRMS (Micromass GCT-MS EI) exact mass calcd for (C 14 H 16 O 5 ) + requires m/z , found m/z (E)-Ethyl 4-(2-formyl-5-methoxyphenoxy)but-2-enoate (1d). 78% yield (Flash column S2
3 chromatography eluent, petroleum ether / ethyl acetate= 70: 1 to 40: 1); yellow solid, mp: o C; 1 H-NMR (CDCl 3, 400 MHz) δ (ppm): 1.31 (t, J= 7.1 Hz, 3H), 3.86 (s, 3H), 4.20 (q, J= 7.1 Hz, 2H), 4.78 (q, J= 2.1 Hz, 2H), (m, 1H), 6.40 (d, J= 2.2 Hz, 1H), (m, 1H), (m, 1H), 7.84 (d, J= 8.7 Hz, 1H), (s, 1H); 13 C NMR (CDCl 3, 101 MHz) δ (ppm): 14.21, 55.71, 60.73, 66.86, 99.06, , , , , , , , , ; IR (KBr): γ 3426, 3072, 2856, 1719, 1671, 1607, 1505, 1427, 1282, 1201, 1172, 1123, 1084, 1039, 957, 882, 811, 647 cm -1 ; HRMS (Micromass GCT-MS EI) exact mass calcd for (C 14 H 16 O 5 ) + requires m/z , found m/z (E)-Ethyl 4-(2-formyl-6-methoxyphenoxy)but-2-enoate (1e). 78% yield (Flash column chromatography eluent, petroleum ether / ethyl acetate= 40: 1 to petroleum ether / ethyl acetate / CH 2 Cl 2 = 30: 1: 1); white solid, mp: o C; 1 H-NMR (CDCl 3, 400 MHz) δ (ppm): 1.25 (t, J= 7.1 Hz, 3H), 3.84 (s, 3H), 4.15 (q, J= 7.1 Hz, 2H), 4.76 (q, J= 1.9 Hz, 2H), (m, 1H), (m, 1H), (m, 1H), (m, 1H), (s, 1H); 13 C NMR (CDCl 3, 101 MHz) δ (ppm): 14.61, 56.49, 60.95, 72.89, , , , , , , , , , ; IR (KBr): γ 3434, 2986, 2904, 1711, 1660, 1586, 1482, 1433, 1305, 1270, 1178, 1073, 1044, 961, 922, 843, 786, 744 cm -1 ; HRMS (Micromass GCT-MS EI) exact mass calcd for (C 14 H 16 O 5 ) + requires m/z , found m/z (E)-Ethyl 4-(2-ethoxy-6-formylphenoxy)but-2-enoate (1f). 78% yield (Flash column chromatography eluent, petroleum ether / ethyl acetate = 70: 1 to 40: 1); white solid, mp: o C; 1 H-NMR (CDCl 3, 400 MHz) δ (ppm): (m, 3H), (m, 3H), (m, 2H), (m, 2H), (m, 2H), (m, 2H), (m, 3H), (m, 1H), (s, 1H); 13 C NMR (CDCl 3, 101 MHz) δ (ppm): 14.24, 14.82, 60.56, 64.75, 72.48, , , , , , , , , , ; IR (KBr): γ 3413, 2986, 2899, 1718, 1697, 1659, 1585, 1480, 1400, 1304, 1279, 1209, 1178, 1065, 958, 924, 869, 782, 746 cm -1 ; HRMS (Micromass GCT-MS EI) exact mass calcd for (C 15 H 18 O 5 ) + requires m/z , found m/z (E)-Ethyl 4-(2-fluoro-6-formylphenoxy)but-2-enoate (1g). 89% yield (Flash column chromatography eluent, petroleum ether / ethyl acetate= 70: 1 to 10: 1); white solid, mp: o C; 1 H-NMR (CDCl 3, 400 MHz) δ (ppm): 1.31 (t, J= 7.1 Hz, 3H), 4.20 (q, J= 7.1 Hz, 2H), (m, 2H), (m, 1H), (m, 1H), (m, 1H), (m, 1H), (s, 1H); 13 C NMR (CDCl 3, 101 MHz) δ (ppm): 14.22, 60.71, (d, J= 7.4 Hz), , (d, J= S3
4 19.3 Hz), (d, J= 3.3 Hz), (d, J= 7.3 Hz), (d, J= 1.6 Hz), , (d, J= 10.7 Hz), (d, J= Hz), , (d, J= 3.3 Hz); IR (KBr): γ 3430, 2986, 2874, 1722, 1690, 1481, 1382, 1303, 1270, 1180, 1078, 1035, 960, 927, 791, 779, 735, 681 cm -1 ; HRMS (Micromass GCT-MS EI) exact mass calcd for (C 13 H 13 FO 4 ) + requires m/z , found m/z (E)-Methyl 4-(2-formylphenoxy)but-2-enoate (1h). 60% yield (Flash column chromatography eluent, petroleum ether / ethyl acetate = 10: 1 to petroleum ether / ethyl acetate / CH 2 Cl 2 =15: 1); white solid, mp: o C; 1 H-NMR (CDCl 3, 400 MHz) δ (ppm): 3.73 (s, 3H), (m, 2H), (m, 1H), 6.79 (d, J= 8.4 Hz, 1H), (m, 2H), (m, 1H), (m, 1H), (s, 1H); 13 C NMR (CDCl 3, 101 MHz) δ (ppm): 52.19, 67.25, 98.77, , , , , , , , , , ; IR (KBr): γ 3426, 2951, 2861, 2766, 1719, 1683, 1599, 1494, 1442, 1390, 1312, 1239, 1165, 1108, 1017, 960, 849, 769, 739, 662, 612 cm -1 ; HRMS (Micromass GCT-MS EI) exact mass calcd for (C 12 H 12 O 4 ) + requires m/z , found m/z General Procedure for the organocatalytic enantioselectivity intramolecular [3+2] reaction. Aldehyde (0.24 mmol), amine (0. 20 mmol), 400mg 3Å MS and catalyst (0.02 mmol) were dissolved in toluene (1 ml), the reaction mixture was stirred at 25 o C for 72 hours. Then filtrate and added the saturated NaHCO 3 to the reaction mixture, extract with CH 2 Cl 2 (10 ml X 3), dry with anhydrous Na 2 SO 4 and rotary evaporate the solvent. The mixture was purified through flash column chromatography on a silica gel (eluent: petroleum ether: ethyl acetate) to give the pure products. (2S,3S,3aS,9bS)-3-Ethyl-2-methyl-2-phenyl-1,2,3,3a,4,9b-hexahydrochromeno[4,3-b]pyrrole-2,3-dicarboxylate (3a) mg (This template reaction was carried out at 0.1 mmol scale and flash column chromatography eluent, petroleum ether to petroleum ether / ethyl acetate = 15: 1), 94% yield; yellow solid; mp: o C; [ ] 20 D = o (c = 0.088, EtOAc); 1 H-NMR (CDCl 3, 400 MHz) δ (ppm): 1.35 (t, J= 7.2 Hz, 3H), (m, 1H), 3.21 (d, J= 11.6 Hz, 1H), 3.31 (s, 1H), 3.63 (s, 3H), 3.68 (bs, 1H), 4.07 (dd, J 1 = 10.2 Hz, J 2 = 11.6 Hz, 1H), (m, 2H), 4.50 (dd, J 1 = 4.2 Hz, J 2 = 10.1 Hz, 1H), (m, 1H), (m, 1H), (m, 1H), (m, 1H), (m, 2H), (m, 1H), (m, 2H); 13 C NMR (CDCl 3, 101 MHz) δ (ppm): 14.20, 49.46, 53.18, 58.78, 60.74, 61.52, 68.99, 77.62, , , , , , , , , , , , ; IR (KBr): γ 3448, 3284, 2960, 17336, 1610, 1489, 1456, 1253, 1179, 1092, 1036, 989, 837, 756, 699 cm -1 ; HRMS (Micromass GCT-MS EI) S4
5 exact mass calcd for (C 22 H 23 NO 5 ) + requires m/z , found m/z ; Enantiomeric excess: 91%, determined by HPLC (Daicel Chirapak AD-H, hexane/ isopropanol = 90: 10, flow rate 1.0 ml/min): T R = 9.55 min (major), T R = min (minor). (2S,3S,3aS,9bS)-3-Ethyl-2-methyl-2-(2-chlorophenyl)-1,2,3,3a,4,9b-hexahydrochromeno[4,3-b] pyrrole-2,3-dicarboxylate (3b) mg (Flash column chromatography eluent, petroleum ether / ethyl acetate = 10: 1), 89% yield; [ ] 20 D = o (c = 1.070, EtOAc); 1 H-NMR (CDCl 3, 400 MHz) δ (ppm): 1.26 (t, J= 7.1 Hz, 3H), (m, 1H), 3.61 (d, J= 12.1 Hz, 1H), 3.64 (s, 3H), 3.74 (bs, 1H), (m, 3H), 4.53 (dd, J 1 = 4.2 Hz, J 2 = 10.0 Hz, 1H), 6.83 (dd, J 1 = 1.0 Hz, J 2 = 8.2 Hz, 1H); (m, 1H), (m, 2H), (m, 3H), (m, 1H), 7.99 (dd, J 1 = 1.8 Hz, J 2 = 7.8 Hz, 1H); 13 C NMR (CDCl 3, 101 MHz) δ (ppm): 14.15, 46.10, 53.48, 55.01, 58.75, 61.50, 68.90, 76.33, , , , , , , , , , , , ; IR (KBr): γ 3448, 3287, 2929, 1739, 1609, 1458, 1330, 1266, 1176, 1038, 984, 848, 758, 747 cm -1 ; HRMS (Micromass GCT-MS EI) exact mass calcd for (C 22 H 22 ClNO 5 ) + requires m/z , found m/z ; Enantiomeric excess: 87%, determined by HPLC (Daicel Chirapak AD-H, hexane/ isopropanol = 90: 10, flow rate 1.0 ml/min): T R = min (major), T R = min (minor). (2S,3S,3aS,9bS)-3-Ethyl-2-methyl-2-(3-chlorophenyl)-1,2,3,3a,4,9b-hexahydrochromeno[4,3-b] pyrrole-2,3-dicarboxylate (3c) mg (Flash column chromatography eluent, petroleum ether / ethyl acetate = 15: 1), 86% yield; white solid, mp: o C; [ ] 20 D = o (c = 0.128, EtOAc); 1 H-NMR (CDCl 3, 400 MHz) δ (ppm): 1.36 (t, J= 7.1 Hz, 3H), (m, 1H), 3.14 (d, J= 11.7 Hz, 1H), 3.31 (d, J= 12.5 Hz, 1H), 3.60 (d, J= 11.7 Hz, 1H), 3.64 (s, 3H), 4.07 (dd, J 1 = 10.2 Hz, J 2 = 11.5 Hz, 1H), (m, 2H), 4.50 (dd, J 1 = 4.2 Hz, J 2 = 10.2 Hz, 1H), 6.83 (dd, J 1 = 0.8 Hz, J 2 = 8.2 Hz, 1H); (m, 1H), (m, 1H), (m, 2H), (m, 1H), (m, 1H), 7.99 (t, J= 1.6 Hz, 1H); 13 C NMR (CDCl 3, 101 MHz) δ (ppm): 14.17, 49.27, 53.37, 58.88, 60.76, 61.66, 68.89, 77.21, , , , , , , , , , , , ; IR (KBr): γ 3296, 2986, 1739, 1597, 1570, 1488, 1458, 1432, 1371, 1250, 1207, 1181, 1036, 995, 833, 759, 698 cm -1 ; HRMS (Micromass GCT-MS EI) exact mass calcd for (C 22 H 22 ClNO 5 ) + requires m/z , found m/z ; Enantiomeric excess: 92%, determined by HPLC (Daicel Chirapak OD-H, hexane/ isopropanol = 85: 15, flow rate 1.0 ml/min): T R = 6.32 min (minor), T R = min (major). (2S,3S,3aS,9bS)-3-Ethyl-2-methyl-2-(4-chlorophenyl)-1,2,3,3a,4,9b-hexahydrochromeno[4,3-b] S5
6 pyrrole-2,3-dicarboxylate (3d) mg (Flash column chromatography eluent, petroleum ether / ethyl acetate = 15: 1), 80% yield; white solid, mp: o C; [ ] 20 D = o (c = 0.110, EtOAc); 1 H-NMR (CDCl 3, 400 MHz) δ (ppm): 1.34 (t, J= 7.1 Hz, 3H), (m, 1H), 3.12 (d, J= 11.6 Hz, 1H), 3.30 (d, J= 12.0 Hz, 1H), 3.59 (d, J= 11.6 Hz, 1H), 3.63 (s, 3H), 4.06 (dd, J 1 = 10.2 Hz, J 2 = 11.6 Hz, 1H), (m, 2H), 4.49 (dd, J 1 = 4.2 Hz, J 2 = 10.2 Hz, 1H), 6.83 (dd, J 1 = 0.8 Hz, J 2 = 8.2 Hz, 1H); (m, 1H), (m, 2H), (m, 1H), (m, 2H); 13 C NMR (CDCl 3, 101 MHz) δ (ppm): 14.20, 49.42, 53.31, 58.87, 60.89, 61.64, 68.92, 77.19, , , , , , , , , , , , ; IR (KBr): γ 3448, 3309, 2926, 1729, 1611, 1492, 1455, 1332, 1254, 1176, 1089, 979, 838, 770 cm -1 ; HRMS (Micromass GCT-MS EI) exact mass calcd for (C 22 H 22 ClNO 5 ) + requires m/z , found m/z ; Enantiomeric excess: 90%, determined by HPLC (Daicel Chirapak OD-H, hexane/ isopropanol = 85: 15, flow rate 1.0 ml/min): T R = 6.69 min (minor), T R = 9.31 min (major). (2S,3S,3aS,9bS)-3-Ethyl-2-methyl-2-(2-fluorophenyl)-1,2,3,3a,4,9b-hexahydrochromeno[4,3-b] pyrrole-2,3-dicarboxylate (3e) mg (Flash column chromatography eluent, petroleum ether / ethyl acetate = 15: 1), 93% yield; [ ] 20 D = o (c = 0.990, EtOAc); 1 H-NMR (CDCl 3, 400 MHz) δ (ppm): 1.29 (t, J= 7.1 Hz, 3H), (m, 1H), 3.26 (dd, J 1 = 1.8 Hz, J 2 = 11.9 Hz, 1H), 3.44 (s, 1H), 3.69 (bs, 4H), (m, 3H), 4.54 (dd, J 1 = 4.2 Hz, J 2 = 10.2 Hz, 1H), 6.83 (dd, J 1 = 0.9 Hz, J 2 = 8.2 Hz, 1H), (m, 1H), (m, 3H); (m, 1H), (m, 1H), (m, 1H); 13 C NMR (CDCl 3, 101 MHz) δ (ppm): 14.22, 48.39, 53.33, 58.38, 58.94, 61.28, 69.19, (d, J= 2.4 Hz), , (d, J= 22.8 Hz), , (d, J= 3.3 Hz), , , (d, J= 3.4 Hz), , (d, J= 8.6 Hz), (d, J= 11.3 Hz), , (d, J= Hz), , ; IR (KBr): γ 3443, 3289, 2929, 1741, 1579, 1479, 1460, 1334, 1303, 1262, 1173, 1033, 979, 823, 763, 747 cm -1 ; HRMS (Micromass GCT-MS EI) exact mass calcd for (C 22 H 22 FNO 5 ) + requires m/z , found m/z ; Enantiomeric excess: 94%, determined by HPLC (Daicel Chirapak OD-H, hexane/ isopropanol = 85: 15, flow rate 1.0 ml/min): T R = 7.82 min (minor), T R = min (major). (2S,3S,3aS,9bS)-3-Ethyl-2-methyl-2-(3-fluorophenyl)-1,2,3,3a,4,9b-hexahydrochromeno[4,3-b] pyrrole-2,3-dicarboxylate (3f) mg (Flash column chromatography eluent, petroleum ether / ethyl acetate = 15: 1), 82% yield; white solid, mp: o C; [ ] 20 D = o (c = 0.154, EtOAc); 1 H-NMR (CDCl 3, 400 MHz) δ (ppm): 1.36 (t, J= 7.2 Hz, 3H), (m, 1H), 3.15 (d, J= 11.6 Hz, 1H), 3.61 (d, J= 11.1 Hz, 1H), 3.64 (s, 3H), 4.07 (dd, J 1 = 10.2 Hz, J 2 = 11.6 Hz, 1H), S6
7 (m, 2H), 4.50 (dd, J 1 = 4.2 Hz, J 2 = 10.2 Hz, 1H), 6.83 (dd, J 1 = 0.9 Hz, J 2 = 8.2 Hz, 1H), (m, 1H), (m, 1H), (m, 1H); (m, 1H), (m, 1H), (m, 2H); 13 C NMR (CDCl 3, 101 MHz) δ (ppm): 14.18, 49.33, 53.33, 58.87, 60.78, 61.65, 68.90, 77.27, (d, J= 1.4 Hz), , , , (d, J= 2.8 Hz), , , , (d, J= 8.0 Hz), (d, J= 7.0 Hz), , (d, J= Hz), , ; IR (KBr): γ 3296, 2951, 1740, 1609, 1591, 1491, 1454, 1250, 1202, 1169, 1036, 995, 831, 755, 688 cm -1 ; HRMS (Micromass GCT-MS EI) exact mass calcd for (C 22 H 22 FNO 5 ) + requires m/z , found m/z ; Enantiomeric excess: 90%, determined by HPLC (Daicel Chirapak OD-H, hexane/ isopropanol = 85: 15, flow rate 1.0 ml/min): T R = 6.13 min (minor), T R = 9.92 min (major). (2S,3S,3aS,9bS)-3-Ethyl-2-methyl-2-(4-fluorophenyl)-1,2,3,3a,4,9b-hexahydrochromeno[4,3-b] pyrrole-2,3-dicarboxylate (3g). 67 mg (Flash column chromatography eluent, petroleum ether / ethyl acetate = 15: 1), 84% yield; white solid, mp: o C; [ ] 20 D = o (c = 0.134, EtOAc); 1 H-NMR (CDCl 3, 400 MHz) δ (ppm): 1.35 (t, J= 7.1 Hz, 3H), (m, 1H), 3.14 (d, J= 11.6 Hz, 1H), 3.31 (d, J= 11.4 Hz, 1H), 3.59 (bs, 1H), 3.63 (s, 3H), 4.07 (dd, J 1 = 10.2 Hz, J 2 = 11.6 Hz, 1H), (m, 2H), 4.49 (dd, J 1 = 4.2 Hz, J 2 = 10.1 Hz, 1H), 6.83 (dd, J 1 = 0.8 Hz, J 2 = 8.2 Hz, 1H); (m, 1H), (m, 2H), (m, 1H), (m, 2H), (m, 2H); 13 C NMR (CDCl 3, 101 MHz) δ (ppm): 14.19, 49.48, 53.24, 58.81, 60.99, 61.60, 68.93, 77.17, (d, J= 21.3 Hz), , , , , , (d, J= 8.0 Hz), (d, J= 3.0 Hz), , (d, J= Hz), , ; IR (KBr): γ 3438, 3277, 2921, 1735, 1610, 1509, 1489, 1461, 1255, 1088, 1038, 994, 848, 815, 758 cm -1 ; HRMS (Micromass GCT-MS EI) exact mass calcd for (C 22 H 22 FNO 5 ) + requires m/z , found m/z ; Enantiomeric excess: 91%, determined by HPLC (Daicel Chirapak OD-H, hexane/ isopropanol = 85: 15, flow rate 1.0 ml/min): T R = 6.18 min (minor), T R = min (major). (2S,3S,3aS,9bS)-3-Ethyl-2-methyl-2-(4-methoxyphenyl)-1,2,3,3a,4,9b-hexahydrochromeno[4,3 -b]pyrrole-2,3-dicarboxylate (3h) mg (Flash column chromatography eluent, petroleum ether / ethyl acetate = 15: 1), 65% yield; colorless oil; [ ] 20 D = o (c = 0.800, EtOAc); 1 H-NMR (CDCl 3, 400 MHz) δ (ppm): 1.34 (t, J= 7.2 Hz, 3H), (m, 1H), 3.16 (d, J= 11.6 Hz, 1H), 3.62 (s, 1H), 3.67 (bs, 1H), 3.81 (s, 3H), 4.07 (dd, J 1 = 10.2 Hz, J 2 = 11.6 Hz, 1H), (m, 2H), 4.49 (dd, J 1 = 4.2 Hz, J 2 = 10.1 Hz, 1H), 6.83 (dd, J 1 = 0.9 Hz, J 2 = 8.2 Hz, 1H), (m, 3H), (m, 1H), (m, 1H); (m, 2H); 13 C NMR (CDCl 3, 101 MHz) δ S7
8 (ppm): 14.21, 49.52, 53.12, 55.27, 58.74, 60.85, 61.47, 69.01, 77.34, , , , , , , , , , , , ; IR (KBr): γ 3451, 3272, 2926, 1738, 1611, 1579, 1510, 1486, 1460, 1246, 1180, 1025, 991, 846, 756 cm -1 ; HRMS (Micromass GCT-MS EI) exact mass calcd for (C 23 H 25 NO 6 ) + requires m/z , found m/z ; Enantiomeric excess: 81%, determined by HPLC (Daicel Chirapak OD-H, hexane/ isopropanol = 70: 30, flow rate 1.0 ml/min): T R = 7.36 min (minor), T R = min (major). (2S,3S,3aS,9bS)-3-Ethyl-2-methyl-8-chloro-2-phenyl-1,2,3,3a,4,9b-hexahydrochromeno[4,3-b] pyrrole-2,3-dicarboxylate (5a) mg (Flash column chromatography eluent, petroleum ether / ethyl acetate = 4: 1), 60% yield; colorless oil; [ ] 20 D = o (c = 0.094, EtOAc); 1 H-NMR (CDCl 3, 400 MHz) δ (ppm): 1.35 (t, J= 7.1 Hz, 3H), (m, 1H), 3.20 (d, J= 11.6 Hz, 1H), 3.28 (d, J= 8.7 Hz, 1H), 3.59 (d, J= 7.9 Hz, 1H), 3.63 (s, 3H), 4.04 (dd, J 1 = 10.2 Hz, J 2 = 11.6 Hz, 1H), (m, 2H), 4.49 (dd, J 1 = 4.3 Hz, J 2 = 10.2 Hz, 1H), 6.75 (d, J= 8.7 Hz, 1H), (m, 1H), (m, 1H), (m, 2H), 7.47 (dd, J 1 = 1.1 Hz, J 2 = 2.6 Hz, 1H), (m, 2H); 13 C NMR (CDCl 3, 101 MHz) δ (ppm): 14.20, 49.07, 53.25, 58.48, 60.54, 61.60, 69.07, 77.54, , , , , , , , , , , , ; IR (KBr): γ 3292, 2981, 1738, 1600, 1483, 1432, 1373, 1255, 1205, 1182, 1101, 1035, 991, 817, 745, 701 cm -1 ; HRMS (Micromass GCT-MS EI) exact mass calcd for (C 22 H 22 ClNO 5 ) + requires m/z , found m/z ; Enantiomeric excess: 53%, determined by HPLC (Daicel Chirapak IA-H, hexane/ isopropanol = 95: 5, flow rate 1.0 ml/min): T R = min (minor), T R = min (major). (2S,3S,3aS,9bS)-3-Ethyl-2-methyl-8-methoxy-2-phenyl-1,2,3,3a,4,9b-hexahydrochromeno[4,3- b]pyrrole-2,3-dicarboxylate (5b) mg (Flash column chromatography eluent, petroleum ether / ethyl acetate = 15: 1), 56% yield; colorless oil; [ ] 20 D = o (c = 0.626, EtOAc); 1 H-NMR (CDCl 3, 400 MHz) δ (ppm): 1.35 (t, J= 7.2 Hz, 3H), (m, 1H), 3.20 (d, J= 11.6 Hz, 1H), 3.30 (s, 1H), 3.63 (bs, 4H), 3.81 (s, 3H), 4.01 (dd, J 1 = 10.2 Hz, J 2 = 11.6 Hz, 1H), (m, 2H), 4.45 (dd, J 1 = 4.2 Hz, J 2 = 10.1 Hz, 1H), (m, 2H), (m, 1H), (m, 1H), (m, 2H); (m, 2H); 13 C NMR (CDCl 3, 101 MHz) δ (ppm): 14.20, 49.62, 53.19, 55.90, 58.99, 60.75, 61.51, 68.65, 77.56, , , , , , , , , , , , ; IR (KBr): γ 3296, 2956, 1732, 1601, 1492, 1432, 1370, 1256, 1203, 1036, 997, 861, 817, 737, 699 cm -1 ; HRMS (Micromass GCT-MS EI) exact mass calcd for (C 23 H 25 NO 6 ) + requires m/z , found m/z ; Enantiomeric excess: 68%, S8
9 determined by HPLC (Daicel Chirapak AD-H, hexane/ isopropanol = 90: 10, flow rate 1.0 ml/min): T R = min (minor), T R = min (major). (2S,3S,3aS,9bS)-3-Ethyl-2-methyl-7-methoxy-2-phenyl-1,2,3,3a,4,9b-hexahydrochromeno[4,3- b]pyrrole-2,3-dicarboxylate (5c) mg (Flash column chromatography eluent, petroleum ether / ethyl acetate = 10: 1), 42% yield; colorless oil; [ ] 20 D = o (c = 0.444, EtOAc); 1 H-NMR (CDCl 3, 400 MHz) δ (ppm): 1.35 (t, J= 7.1 Hz, 3H), (m, 1H), 3.19 (d, J= 11.6 Hz, 1H), 3.24 (s, 1H), 3.57 (d, J= 11.7 Hz, 1H), 3.62 (s, 3H), 3.76 (s, 3H), 4.04 (dd, J 1 = 10.2 Hz, J 2 = 11.6 Hz, 1H), (m, 2H), 4.48 (dd, J 1 = 4.2 Hz, J 2 = 10.1 Hz, 1H), 6.41 (d, J= 2.4 Hz, 1H), 6.51 (dd, J 1 = 2.5 Hz, J 2 = 8.4 Hz, 1H), (m, 1H), (m, 3H); (m, 2H); 13 C NMR (CDCl 3, 101 MHz) δ (ppm): 14.20, 49.92, 53.16, 55.34, 58.48, 60.62, 61.49, 69.08, 77.69, , , , , , , , , , , , ; IR (KBr): γ 3296, 2956, 1738, 1622, 1579, 1508, 1443, 1373, 1322, 1257, 1159, 1036, 856, 793, 699, 635 cm -1 ; HRMS (Micromass GCT-MS EI) exact mass calcd for (C 23 H 25 NO 6 ) + requires m/z , found m/z ; Enantiomeric excess: 90%, determined by HPLC (Daicel Chirapak OD-H, hexane/ isopropanol = 95: 5, flow rate 1.0 ml/min): T R = min (major), T R = min (minor). (2S,3S,3aS,9bS)-3-Ethyl-2-methyl-6-methoxy-2-phenyl-1,2,3,3a,4,9b-hexahydrochromeno[4,3- b]pyrrole-2,3-dicarboxylate (5d). 44 mg (Flash column chromatography eluent, petroleum ether / ethyl acetate = 8: 1), 54% yield; colorless oil; [ ] 20 D = o (c = 0.558, EtOAc); 1 H-NMR (CDCl 3, 400 MHz) δ (ppm): 1.34 (t, J= 7.1 Hz, 3H), (m, 1H), 3.21 (d, J= 11.6 Hz, 1H), 3.30 (s, 1H), 3.62 (s, 3H), 3.69 (d, J= 19.8 Hz, 1H), 3.87 (s, 3H), 4.13 (dd, J 1 = 10.2 Hz, J 2 = 16.7 Hz, 1H), (m, 2H), 4.64 (dd, J 1 = 4.2 Hz, J 2 = 10.1 Hz, 1H), (m, 1H), (m, 1H), (m, 2H), (m, 1H); (m, 2H), (m, 2H); 13 C NMR (CDCl 3, 101 MHz) δ (ppm): 14.18, 49.23, 53.17, 55.93, 58.66, 60.80, 61.52, 69.49, 77.53, , , , , , , , , , , , ; IR (KBr): γ 3430, 3292, 2929, 1738, 1581, 1486, 1460, 1254, 1208, 1179, 1085, 1070, 1023, 993, 853, 740, 701 cm -1 ; HRMS (Micromass GCT-MS EI) exact mass calcd for (C 23 H 25 NO 6 ) + requires m/z , found m/z ; Enantiomeric excess: 70%, determined by HPLC (Daicel Chirapak AD-H, hexane/ isopropanol = 97: 3, flow rate 1.0 ml/min): T R = min (major), T R = min (minor). (2S,3S,3aS,9bS)-3-Ethyl-2-methyl-6-ethoxy-2-phenyl-1,2,3,3a,4,9b-hexahydrochromeno[4,3-b] S9
10 pyrrole-2,3-dicarboxylate (5e) mg (Flash column chromatography eluent, petroleum ether / ethyl acetate = 10: 1), 76% yield; colorless oil; [ ] 20 D = o (c = 0.088, EtOAc); 1 H-NMR (CDCl 3, 400 MHz) δ (ppm): 1.34 (t, J= 7.1 Hz, 3H), 1.45 (t, J= 7.0 Hz, 3H), (m, 1H), 3.21 (d, J= 11.6 Hz, 1H), 3.30 (s, 1H), 3.62 (s, 3H), 3.66 (bs, 1H), (m, 3H), (m, 2H), 4.64 (dd, J 1 = 4.2 Hz, J 2 = 10.1 Hz, 1H), (m, 2H), (m, 1H), (m, 1H), (m, 2H), (m, 2H); 13 C NMR (CDCl 3, 101 MHz) δ (ppm): 14.20, 14.82, 49.25, 53.16, 58.77, 60.84, 61.51, 64.33, 69.44, 77.56, , , , , , , , , , , , ; IR (KBr): γ 3434, 3292, 2977, 1739, 1716, 1579, 1457, 1335, 1250, 1183, 1087, 1063, 984, 850, 754, 725, 702 cm -1 ; HRMS (Micromass GCT-MS EI) exact mass calcd for (C 24 H 27 NO 6 ) + requires m/z , found m/z ; Enantiomeric excess: 78%, determined by HPLC (Daicel Chirapak AD-H, hexane/ isopropanol = 90: 10, flow rate 1.0 ml/min): T R = min (major), T R = min (minor). (2S,3S,3aS,9bS)-3-Ethyl-2-methyl-6-fluoro-2-phenyl-1,2,3,3a,4,9b-hexahydrochromeno[4,3-b] pyrrole-2,3-dicarboxylate (5f) mg (Flash column chromatography eluent, petroleum ether / ethyl acetate = 10: 1), 63% yield; white solid; mp: o C; [ ] 20 D = o (c = 0.114, EtOAc); 1 H-NMR (CDCl 3, 400 MHz) δ (ppm): 1.35 (t, J= 7.1 Hz, 3H), (m, 1H), 3.23 (d, J= 11.6 Hz, 1H), 3.32 (s, 1H), 3.63 (s, 3H), 3.68 (bs, 1H), 4.12 (dd, J 1 = 10.2 Hz, J 2 = 11.7 Hz, 1H), (m, 2H), 4.62 (dd, J 1 = 4.3 Hz, J 2 = 10.2 Hz, 1H), (m, 1H), (m, 1H), (m, 1H), (m, 1H); (m, 2H), (m, 2H); 13 C NMR (CDCl 3, 101 MHz) δ (ppm): 14.19, 49.11, 53.24, (d, J= 3.1 Hz), 60.59, 61.62, 69.53, 77.45, (d, J= 18.1 Hz), , (d, J= 3.3 Hz), (d, J= 1.6 Hz), , , , (d, J= 10.2 Hz), , (d, J= Hz), , ; IR (KBr): γ 3305, 2956, 2844, 1737, 1579, 1480, 1468, 1430, 1382, 1334, 1274, 1255, 1172, 1068, 983, 848, 785, 739, 698 cm -1 ; HRMS (Micromass GCT-MS EI) exact mass calcd for (C 22 H 22 FNO 5 ) + requires m/z , found m/z ; Enantiomeric excess: 68%, determined by HPLC (Daicel Chirapak OD-H, hexane/ isopropanol = 95: 5, flow rate 1.0 ml/min): T R = 8.97 min (minor), T R = min (major). (2S,3S,3aS,9bS)-Dimethyl-2-phenyl-1,2,3,3a,4,9b-hexahydrochromeno[4,3-b]pyrrole-2,3-dicar boxylate (5g). 46 mg (Flash column chromatography eluent, petroleum ether / ethyl acetate = 10: 1), 84% yield; white solid; mp: o C; [ ] 20 D = o (c = 0.108, EtOAc); 1 H-NMR (CDCl 3, 400 MHz) δ (ppm): (m, 1H), 3.23 (d, J= 11.6 Hz, 1H), 3.32 (s, 1H), 3.63 (s, 3H), 3.68 (bs, 1H), 3.80 (s, 3H), 4.05 (dd, J 1 = 10.2 Hz, J 2 = 11.6 Hz, 1H), 4.49 (dd, J 1 = 4.2 Hz, J 2 = 10.1 Hz, 1H), S10
11 (m, 1H), (m, 1H), (m, 1H), (m, 1H), (m, 2H), (m, 1H), (m, 2H); 13 C NMR (CDCl 3, 101 MHz) δ (ppm): 49.46, 52.52, 53.28, 58.79, 60.55, 68.90, 77.78, , , , , , , , , , , , ; IR (KBr): γ 3460, 3279, 2956, 1735, 1611, 1581, 1490, 1455, 1432, 1254, 1182, 1036, 989, 843, 761, 701 cm -1 ; HRMS (Micromass GCT-MS EI) exact mass calcd for (C 21 H 21 NO 5 ) + requires m/z , found m/z ; Enantiomeric excess: 74%, determined by HPLC (Daicel Chirapak AD-H, hexane/ isopropanol = 90: 10, flow rate 1.0 ml/min): T R = 9.89 min (major), T R = min (minor). References: 1. (a) Chen, X. H.; Wei, Q.; Luo, S. W.; Xiao, H.; Gong, L. Z. J. Am. Chem. Soc. 2009, 131, Other group had also been reported this catalyst, see: (b) Storer, R. I.; Carrera, D. E.; Ni, Y.; MacMillan, D.W. C. J. Am. Chem. Soc. 2006, 128, 84. (c) Reuping, M.; Sugiono, E.; Azap, C.; Theissmann, T.; Bolte, M. Org. Lett. 2005, 7, (d) Hoffman, S.; Seayad, A. M.; List, B. Angew. Chem.Int. Ed. 2005, 44, S11
12 X-ray single crystal data for 3d : O HN COOCH 2 CH 3 COOCH 3 3d Cl X-ray crystal structure of 3d with ellipsoids set at 45% probability. Hydrogen atoms are omitted for clarity. Chemical formula C22 H22 Cl N O5 Formula weight Space group P 21 Z 2 a Å (10) b, Å (13) c, Å (17) V, Å (2) T, K 291,g/cm CCDC number: S12
13 Selected NMR and HPLC spectra S13
14 S14
15 S15
16 S16
17 S17
18 S18
19 S19
20 S20
21 S21
22 S22
23 S23
24 S24
25 S25
26 S26
27 S27
28 S28
29 S29
30 S30
31 S31
32 S32
33 S33
34 S34
35 O HN COOEt COOMe S35
36 O HN COOEt COOMe F S36
37 O HN COOEt COOMe Cl S37
38 O HN COOEt COOMe Cl S38
39 O HN COOEt COOMe F S39
40 O HN COOEt COOMe F S40
41 MeO O HN COOEt COOMe S41
42 OMe O HN COOEt COOMe S42
43 OEt O HN COOEt COOMe S43
44 O HN COOEt COOMe OMe S44
45 O HN COOMe COOMe S45
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
Electronic 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
Supporting 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
A 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
Copper-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
Supporting 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
Room 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
Supporting 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
Copper-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
Supporting 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
Supporting 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
Supporting 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
Supporting 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
Facile 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
and 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
The 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
Supporting 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, *
Supporting 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
Tributylphosphine-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
Lewis 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
Chiral 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
Supporting Information for
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2015 Supporting Information for Catalytic Asymmetric Chemoselective 1,3-Dipolar Cycloadditions of Azomethine
Supporting 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
Supporting 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
Direct 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
Eco-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-
Enantioselective 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,
Supporting 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,
Site-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,
Hiyama 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
Mandelamide-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,
Highly 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
Supporting Information
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2018 Supporting Information Silver or Cerium-Promoted Free Radical Cascade Difunctionalization
Vilsmeier 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
Metal-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:
Free 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
Protease-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,
Supplementary 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
Supplementary Figure S1. Single X-ray structure 3a at probability ellipsoids of 20%.
Supplementary Figure S1. Single X-ray structure 3a at probability ellipsoids of 20%. S1 Supplementary Figure S2. Single X-ray structure 5a at probability ellipsoids of 20%. S2 H 15 Ph Ac Ac I AcH Ph Ac
Ligand-free Cu(II)-mediated aerobic oxidations of aldehyde. hydrazones leading to N,N -diacylhydrazines and 1,3,4-oxadiazoles
Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2017 Ligand-free Cu(II)-mediated aerobic oxidations of aldehyde hydrazones leading
The 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
Supporting 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
Regioselectivity 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
Rh(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,
Novel and Selective Palladium-Catalyzed Annulation of 2-Alkynylphenols to Form 2-Substituted 3-Halobenzo[b]furans. Supporting Information
![Novel and Selective Palladium-Catalyzed Annulation of 2-Alkynylphenols to Form 2-Substituted 3-Halobenzo[b]furans. Supporting Information](/thumbs/64/50937700.jpg "Novel and Selective Palladium-Catalyzed Annulation of 2-Alkynylphenols to Form 2-Substituted 3-Halobenzo[b]furans. Supporting Information")
Novel and Selective Palladium-Catalyzed Annulation of 2-Alkynylphenols to Form 2-Substituted 3-Halobenzo[b]furans Liang Yun, Shi Tang, Xu-Dong Zhang, Li-Qiu Mao, Ye-Xiang Xie and Jin-Heng Li* Key Laboratory
Iodine-catalyzed synthesis of sulfur-bridged enaminones and chromones via double C(sp 2 )-H thiolation
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2017 Iodine-catalyzed synthesis of sulfur-bridged enaminones and chromones via
Cu(I)-Catalyzed Asymmetric Multicomponent Cascade Inverse. Electron-Demand aza-diels-alder/nucleophilic Addition/Ring-Opening
Cu(I)-Catalyzed Asymmetric Multicomponent Cascade Inverse Electron-Demand aza-diels-alder/nucleophilic Addition/Ring-Opening Reaction Involving 2-Methoxyfurans as Efficient Dienophiles Rong Huang, Xin
Supporting 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
Construction of Cyclic Sulfamidates Bearing Two gem-diaryl Stereocenters through a Rhodium-Catalyzed Stepwise Asymmetric Arylation Protocol
Supporting Information for: Construction of Cyclic Sulfamidates Bearing Two gem-diaryl Stereocenters through a Rhodium-Catalyzed Stepwise Asymmetric Arylation Protocol Yu-Fang Zhang, Diao Chen, Wen-Wen
ESI 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
gem-dichloroalkenes for the Construction of 3-Arylchromones
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2015 Pd(OAc)2/S=PPh3 Accelerated Activation of gem-dichloroalkenes for the Construction of 3-Arylchromones
Divergent 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,
First 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
9-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
Oxyhalogenation 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
Supporting 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,,*
Supporting 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,
Direct 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](/thumbs/87/95187440.jpg "Direct 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
Fluorinative 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
Supporting 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
Copper-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,
Supporting 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
Electronic 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
Phosphorus 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
Catalyst-free transformation of levulinic acid into pyrrolidinones with formic acid
Catalyst-free transformation of levulinic acid into pyrrolidinones with formic acid Yawen Wei, a Chao Wang,* a Xue Jiang, a Dong Xue, a Zhao-Tie Liu, a and Jianliang Xiao* a,b a Key Laboratory of Applied
Supporting Information. Copyright Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2008
Supporting Information Copyright Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 2008 Rhodium-Catalyzed Cyclopropanation of Alkenes with Diazomalonates Francisco González-Bobes, a * Michaël D. B. Fenster,
Asymmetric 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
Supporting 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
Supporting Information
Supporting Information Metal-catalyzed Stereoselective and Protecting-group-free Synthesis of 1,2-cis-Glycosides Using 4,6-Dimethoxy-1,3,5-triazin-2-yl Glycosides as Glycosyl Donors Tomonari Tanaka,* 1
Supporting Information for
Supporting Information for A ovel Synthesis of luorinated Pyrazoles via Gold(I)-Catalyzed Tandem Aminofluorination of Alkynes in the Presence of Selectfluor Jianqiang Qian, Yunkui Liu,* Jie Zhu, Bo Jiang,
Supporting 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,
Supporting 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 *
Supporting 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
Diastereo- 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
SUPPLEMENTARY INFORMATION
SUPPLEMETARY IFRMATI DI: 10.1038/CEM.1406 ighly enantioselective trapping of zwitterionic intermediates by imines uang Qiu,a, Ming Li,a, Li-Qin Jiang a, Feng-Ping Lv a, Li Zan a, Chang-Wei Zhai a, Michael.
Xiangya International Academy of Translational Medicine, Central South University, 172 Tongzipo Rd., Changsha, Hunan province, China,
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2016 Supporting Information Enantioselective Oxidative Functionalization of Csp3-H Bond Adjacent to
SUPPORTING INFORMATION. 1. General... S1. 2. General procedure for the synthesis of compounds 3 and 4 in the absence of AgOAc...
SUPPORTING INFORMATION Table of contents 1. General.... S1 2. General procedure for the synthesis of compounds 3 and 4 in the absence of AgOAc... S2 3. General procedure for the synthesis of compounds
Copper-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:
Supporting Information
Supporting Information Palladium-Catalyzed Asymmetric Benzylic Substitution of Secondary Benzyl Carbonates with Nitrogen and Oxygen Nucleophiles Atifah Najib, Koji Hirano,* and Masahiro Miura* Department
Aminofluorination 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,
Electronic 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*
Supplementary 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
Copper-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
A New Type of Bis(sulfonamide)-Diamine Ligand for a Cu(OTf) 2 -Catalyzed Asymmetric Friedel-Crafts Alkylation Reaction of Indoles with Nitroalkenes
A ew Type of Bis(sulfonamide)-Diamine Ligand for a Cu(OTf) 2 -Catalyzed Asymmetric Friedel-Crafts Alkylation Reaction of Indoles with itroalkenes Jing Wu, Xincheng Li, Fan Wu, and Boshun Wan* Dalian Institute
Supporting 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,
Supporting 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
Pd 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
Supporting Information
Supporting Information Rhodium-catalyzed Intramolecular Dehydrogenative Aryl Aryl Coupling Using Air as Terminal Oxidant Hannah Baars, 1,2 Yuto Unoh, 1 Takeshi Okada, 1 Koji Hirano, 1 Tetsuya Satoh,* 1,3
Supporting 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
Supplementary Material
Supplementary Material Chiral N-aryl tert-butanesulfinamide-olefin ligands for rhodium-catalyzed asymmetric 1,4-addition Shuai Yuan, Qingle Zeng,* Jiajun Wang, Lihong Zhou State Key Laboratory of Geohazard
Supporting Information. A catalyst-free multicomponent domino sequence for the. diastereoselective synthesis of (E)-3-[2-arylcarbonyl-3-
Supporting Information for A catalyst-free multicomponent domino sequence for the diastereoselective synthesis of (E)-3-[2-arylcarbonyl-3- (arylamino)allyl]chromen-4-ones Pitchaimani Prasanna 1, Pethaiah
Supporting Information for: Intramolecular Hydrogen Bonding-Assisted Cyclocondensation of. 1,2,3-Triazole Synthesis
Supporting Information for: Intramolecular Hydrogen Bonding-Assisted Cyclocondensation of α-diazoketones with Various Amines: A Strategy for Catalytic Wolff 1,2,3-Triazole Synthesis Zikun Wang, a Xihe
Supporting Information for
Supporting Information for Palladium-Catalyzed C-H Bond Functionalization of C6-Arylpurines Hai-Ming Guo,* Wei-Hao Rao, Hong-Ying iu, Li-Li Jiang, Ge ng, Jia-Jia Jin, Xi-ing Yang, and Gui-Rong Qu* College
The Supporting Information for
The Supporting Information for Synthesis of Azacyclic ucleoside Analogues via Asymmetric [3+2] Cycloaddition of 9-(2-tosylvinyl)-9H-purines Dan-Jie Zhang, Ming-Sheng Xie,* Gui-Rong Qu, Yao-Wei Gao, and
Synthesis of novel 1,2,3-triazolyl derivatives of pregnane, androstane and D-homoandrostane. Tandem Click reaction/cu-catalyzed D-homo rearrangement
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2014 Supporting Information Synthesis of novel 1,2,3-triazolyl derivatives of
Supporting Information for Synthesis of Fused N-Heterocycles via Tandem C-H Activation
This journal is The Royal Society of Chemistry 212 Supporting Information for Synthesis of Fused -Heterocycles via Tandem C-H Activation Ge Meng, Hong-Ying iu, Gui-Rong Qu, John S. Fossey, Jian-Ping Li,*
Supporting 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
Supporting Information. Microwave-assisted construction of triazole-linked amino acid - glucoside conjugates as novel PTP1B inhibitors
Supporting Information Microwave-assisted construction of triazole-linked amino acid - glucoside conjugates as novel PTP1B inhibitors Xiao-Peng He, abd Cui Li, d Xiao-Ping Jin, b Zhuo Song, b Hai-Lin Zhang,
Palladium-Catalyzed C H Monoalkoxylation of α,β-unsaturated Carbonyl Compounds
Supporting Information Palladium-Catalyzed C H Monoalkoxylation of α,β-unsaturated Carbonyl Compounds Yasunari Monguchi,* Kouki Kunishima, Tomohiro Hattori, Tohru Takahashi, Yuko Shishido, Yoshinari Sawama,
Efficient and Simple Zinc mediated Synthesis of 3 Amidoindoles
Electronic Supplementary Material (ESI) for rganic and Biomolecular Chemistry SUPPRTIG IFRMATI Efficient and Simple Zinc mediated Synthesis of 3 Amidoindoles Anahit Pews-Davtyan and Matthias Beller* Leibniz-Institut