Supporting Information
|
|
|
- Αδώνια Ασπάσιος
- 5 χρόνια πριν
- Προβολές:
Transcript
1 Supporting Information Wiley-VCH Weinheim, Germany
2 Supporting Information for Catalytic Enantioselective Conjugate Reduction of β,β- Disubstituted α,β-unsaturated sulfones Tomás Llamas, Ramón Gómez Arrayás, and Juan C. Carretero* Departamento de Química Orgánica. Facultad de Ciencias. Universidad Autónoma de Madrid. Cantoblanco Madrid. Spain. Table of Contents 1. EXPERIMENTAL SECTION.. S 2 - General Methods... S 2 - Synthesis of methyl 2-pyridyl sulfone... S 2 - Typical procedure for the synthesis of b,b-disubstituted a,b-unsaturated sulfones... S 3 - Typical procedure for the asymmetric conjugate reduction... S 6 - Protocols for functionalization/desulfonylation... S NMR SPECTRA OF NEW COMPOUNDS... S 14 S 1
3 1. EXPERIMENTAL SECTION General methods All the reactions were carried out in anhydrous solvents and under argon atmosphere. Melting points were taken in open-end capillary tubes. NMR spectra were recorded at 300 MHz ( 1 H), 75 MHz ( 13 C), at room temperature in CDCl 3 [calibrated at 7.26 ppm ( 1 H), and 77.0 ppm ( 13 C)]. Mass spectra (MS) were determined under electospray ionization (ESI). HPLC experiments were conducted using a Chiralpak IA column. Flash column chromatography was performed using silica gel Merk-60 ( mesh). Below are the structures of the chiral ligands considered in the screening test to optimize the enantioselectivity of the conjugate reduction. (R)-Binap t-bu O OMe O Ph 2 P PPh 2 O P t-bu 2 O PPh 2 PCy 2 PPh 2 Fe PPh 2 NMe O P t-bu O PPh 2 2 Fe PPh 2 O OMe t-bu (R)-DTBM-Segphos 2 O (R)-Segphos (R,S)-Josiphos Taniaphos Synthesis of methyl 2-pyridyl sulfone DBU (1.1 eq.) MeI (1.1 eq.) N SH THF:CH 3 CN N SMe 0 ºC 25 ºC H 2 O 2 (3 eq.) Na 2 WO 4 2H 2 O (10 mol%) AcOEt:H 2 O (10:1) I, 92% 99% N SO 2 Me To a solution of 2-mercaptopyridine (5.0 g, 45 mmol) in THF (90 ml) and CH 3 CN (9 ml), 1 cooled to 0 ºC, was added DBU (6.6 ml, 49.5 mmol). The resulting mixture was stirred at 0 ºC for 5 min before MeI (3.1 ml, 49.5 mmol) was slowly added. Then, the ice bath was removed and the mixture was stirred for 4 h. The reaction mixture was washed with water (40 ml) and the aqueous layer was extracted with EtOAc (2 x 40 ml). The combined organic layers were dried (MgSO 4 ), filtered and concentrated. The residue was purified by flash chromatography (n-hexane-etoac 2:1) to afford the methyl 2-pyridyl sulfide (I) as a colourless oil; yield: 5.20 g (92%). 1 H NMR (300 MHz): d 8.42 (m, 1H), 7.47 (m, 1H), 7.16 (m, 1H), 6.96 (m, 1H), 2.55 (s, 3H). 13 C NMR (75 MHz): d 159.9, 149.3, 135.6, 121.3, 119.0, CH 3 CN was added to improve solubility of the sulfone S 2
4 To a solution of I (5.0 g, 39.9 mmol) in EtOAc (50 ml) was added H 2 O (6 ml) and Na 2 WO 4 2H 2 O (1.3 g, 4.0 mmol). The resulting mixture was cooled to 0 ºC before a 30% solution of H 2 O 2 (12.9 ml, 120 mmol) was added dropwise. The reaction was stirred at 0 ºC for 30 min and at rt for 1 h. Then it was cooled to 0 ºC and aqueous saturated NaHSO 3 (10 ml) was added slowly. The organic layer was separated and the aqueous layer was extracted with EtOAc (2 x 20 ml). The combined organic layers were dried (MgSO 4 ), filtered and concentrated. The residue was purified by flash chromathograpy (n-hexane-etoac 2:1) to afford the sulfone as a colourless oil; yield: 6.3 g (99%). 1 H NMR (300 MHz): d (m, 1H), (m, 2H), (m, 1H), 3.21 (s, 3H). 13 C NMR (75 MHz): d 157.8, 149.9, 138.3, 127.4, 121.0, Typical procedure for the synthesis of b,b-disubstituted a,b-unsaturated sulfones: (E)-2-Phenyl-1-phenylsulfonyl-1-propene (1). To a solution of 3.2 mmol of methyl phenyl sulfone (0.5 g) in THF (20 ml), cooled to - 78 ºC, was added a 2.5 M solution of n-buli in hexane (1.4 ml, 3.5 mmol). The mixture was stirred at -78 ºC for 30 min before acetophenone (388 µl, 3.5 mmol) was added. The resulting orange solution was stirred at -78 ºC for 90 min, and then it was treated with aqueous saturated NH 4 Cl (10 ml). The organic layer was separated and the aqueous layer was extracted with EtOAc (2 x 20 ml). The combined organic layers were dried (MgSO 4 ), filtered and concentrated. The crude resulting alcohol and DMAP (40 mg, 0.3 mmol) were dissolved in CH 2 Cl 2 (15 ml). The mixture was cooled to 0 ºC before Et 3 N (892 µl, 6.4 mmol) and TFAA (534 µl, 3.8 mmol) were successively added. The reaction mixture was stirred at 0 ºC for 30 min, allowed to reach rt and stirred at rt overnight. After hydrolysis with aqueous saturated NH 4 Cl (10 ml). The organic layer was separated and the aqueous layer was extracted with CH 2 Cl 2. The combined organic layers were dried (MgSO 4 ), filtered and concentrated. The residue was purified by flash chromatography (n-hexane-etoac 2:1) to afford the sulfone as a white solid; yield: 0.58 g (70%); mp = ºC. 1 H NMR (300 MHz): d (m, 1H), (m, 1H), (m, 3H), (m, 5H), 6.61 (q, J= 1.1 Hz, 1H), 2.54 (d, J= 1.1 Hz, 3H). 13 C NMR (75 MHz): d?153.4, 142.1, 140.0, 133.1, 129.8, 129.1, 128.6, 127.3, 127.1, 126.2, (E)-2-Phenyl-1-[(2-pyridyl)sulfonyl)]-1-propene (2a). White solid; mp = ºC; yield: 0.52 g (63%). 1 H NMR (300 MHz): d 8.74 (ddd, J= 0.9, 1.7, 7.7 Hz, 1H), 8.17 (dt, J= 0.9, 7.7 Hz, 1H), 8.01 (dt, J= 1.7, 7.7 Hz, 1H), 7.57 (ddd, J= 1.0, 4.6, 7.8 Hz, S 3
5 1H), (m, 5H), 6.74 (q, J= 1.0 Hz, 1H), 2.57 (d, J= 1.0 Hz, 3H). 13 C NMR (75 MHz): d?159.4, 155.0, 140.0, 138.0, 130.0, 128.7, 127.0, 126.3, 124.8, 121.7, HRMS (FAB+) Calcd for C 14 H 14 NO 2 S, ; found, (E)-2-(p-Methoxyphenyl)-1-[(2-pyridyl)sulfonyl)]-1-propene (2b). Yellow solid; mp = ºC; yield: 0.64 g (69%). 1 H NMR (300 MHz): d (m, 1H), (m, 1H), 7.95 (dt, J= 1.7, 7.7 Hz, 1H), 7.57 (ddd, J= 1.1, 4.5, 7.7 Hz, 1H), 7.43 (d, J= 9.0, 2H), 6.88 (d, J= 9.0, 2H), 6.72 (q, J= 1.0 Hz, 1H), 3.58 (s, 3H), 2.57 (d, J= 1.0 Hz, 3H). 13 C NMR (75 MHz): δ 161.2, 159.7, 155.3, 150.2, 137.9, 131.9, 127.9, 126.8, 122.8, 121.6, 114.0, 55.3, (E)-2-(p-Nitrophenyl)-1-[(2-pyridyl)sulfonyl)]-1-propene (2c). Yellow solid; mp = ºC; yield: 0.65 g (66%). 1 H NMR (300 MHz): δ (m, 1H), 8.22 (d, J= 8.9 Hz, 2H), (m, 1H), 7.99 (dt, J= 1.7, 7.7 Hz, 1H), (m, 3H), 6.83 (q, J= 1.2 Hz, 1H), 2.61 (d, J= 1.2 Hz, 3H). 13 C NMR (75 MHz): δ 158.9, 153.2, 150.3, 148.4, 146.4, 138.2, 127.8, 127.4, 127.3, 123.9, 121.8, (E)-2-(p-Bromophenyl-1-[(2-pyridyl)sulfonyl)]-1-propene (2d). Yellow solid; mp = ºC; yield: 0.66 g (61%). 1 H NMR (300 MHz): d (m, 1H), (m, 1H), 7.97 (dt, J= 1.7, 7.7 Hz, 1H), (m, 3H), 7.31 (d, J= 8.7, 2H), 6.76 (q, J= 1.0 Hz, 1H), 2.57 (d, J= 1.0 Hz, 3H). 13 C NMR (75 MHz): δ 159.3, 154.5, 150.3, 138.9, 138.1, 131.9, 127.9, 127.1, 125.3, 124.4, 121.7, (E)-2-[(p-Trifluoromethyl)phenyl]-1-[(2-pyridyl)sulfonyl)]-1-propene (2e). White solid; mp = ºC; yield: 0.42 g (51%). 1 H NMR (300 MHz): δ?8.75 (ddd, J= 0.9, 1.7, 4.7 Hz, 1H), 8.17 (dt, J= 1.0, 7.9 Hz, 1H), 7.98 (dt, J= 1.7, 7.8 Hz, 1H), (m, 2H), (m, 3H), 6.80 (q, J= 1.2 Hz, 1H), 2.61 (d, J= 1.2 Hz, 3H). 13 C NMR (75 MHz): δ?159.0, 154.2, 150.3, 143.7, 138.2, (q, J C-F = 32.5 Hz), 127.2, 126.8, 126.7, (q, J C-F = 3.9 Hz), 121.7, (E)-2-(o-Methylphenyl)-1-[(2-pyridyl)sulfonyl)]-1-propene (2f). White solid; mp = ºC; yield: 0.39 g (44%). 1 H NMR (300 MHz): δ 8.73 (ddd, J= 0.9, 1.7, 4.7 Hz, 1H), 8.13 (dt, J= 0.9, 7.8 Hz, 1H), 7.96 (dt, J= 1.7 y 7.7 Hz, 1H), 7.53 (ddd, J= 1.4, 4.6, 7.7 Hz, 1H), (m, 3H), (m, 1H), 6.38 (q, J= 1.3 Hz, 1H), 2.45 (d, J= 1.3 Hz, 3H), 2.21 (s, 3H). 13 C NMR (75 MHz): δ 159.3, 158.4, 150.1, 141.5, 138.0, 133.6, 130.5, 128.3, 127.0, 126.8, 126.5, 125.7, 121.4, 20.2, S 4
6 (E)-2-(o-Bromophenyl-1-[(2-pyridyl)sulfonyl)]-1-propene (2g). White solid; mp = ºC; yield: 0.48 g (45%). 1 H NMR (300 MHz): δ (m, 1H), (m, 1H), 7.99 (dt, J= 1.8, 7.7 Hz, 1H), (m, 2H), (m, 1H), (m, 2H), 6.49 (q, J= 1.3 Hz, 1H), 2.54 (d, J= 1.3 Hz, 3H). 13 C NMR (75 MHz): δ 159.1, 157.1, 150.3, 142.6, 138.0, 133.1, 129.8, 128.5, 128.3, 127.5, 127.1, 121.8, 120.2, (E)-2-(2-Naphtyl)-1-[(2-pyridyl)sulfonyl)]-1-propene (2h). White solid; mp = ºC; yield: 0.58 g (59%). 1 H NMR (300 MHz): δ (m, 1H), (m, 1H), (m, 2H), (m, 3H), (m, 4H), 6.91 (q, J= 1.2 Hz, 1H), 2.70 (d, J= 1.2 Hz, 3H). 13 C NMR (75 MHz): δ 159.5, 155.7, 150.3, 138.1, 137.1, 133.8, 132.9, 128.6, 128.4, 127.5, 127.2, 127.0, 126.7, 126.4, 125.1, 123.4, 121.7, (E)- and (Z)-2-Phenyl-1-[(2-pyridyl)sulfonyl)]-1-butene [(E)-4 and (Z)-4). Purification of the crude mixture by flash chromatography (n-hexane-etoac 2:1) provided (E)-4 (0.26 g, 29%), followed by (Z)-4 (0.24 g, 27%), both as yellow oils. (E)- 4: 1 H NMR (300 MHz): δ (m, 1H), (m, 1H), 7.96 (dt, J= 1.6, 7.8 Hz, 1H), (m, 1H), (m, 5H), 6.64 (s, 1H), 3.11 (q, J= 7.7 Hz, 2H), 0.99 (t, J= 7.7 Hz, 3H). 13 C NMR (75 MHz): δ 162.1, 159.4, 150.2, 138.7, 138.0, 129.7, 128.6, 126.9, 126.7, 124.5, 121.6, 24.0, (Z)-4: 1 H NMR (300 MHz): δ (m, 1H), 7.60 (dt, J= 1.7, 7.7 Hz, 1H), 7.45 (d, J= 7.7 Hz, 1H), (m, 1H), (m, 3H), (m, 2H), 6.71 (t, J= 1.3 Hz, 1H), 2.46 (dq, J= 1.3, 7.5 Hz, 2H), 1.06 (t, J= 7.5 Hz, 3H). 13 C NMR (75 MHz): δ 161.2, 158.4, 149.6, 137.2, 136.7, 127.9, 127.5, 127.2, 126.4, 125.7, 122.0, 33.7, (E)- and (Z)-2-Methyl-1-[(2-pyridyl)sulfonyl)]-3-tetrahydropyranoxy-1-propene [(E)-5 and (Z)-5]. Purification of the crude mixture by flash chromatography (nhexane-etoac 2:1) provided (E)-5 (0.21 g, 22%), followed by (Z)-5 (0.25 g, 26%), both as colorless oils. (E)-5: 1 H NMR (300 MHz): δ 8.70 (d, J= 4.6 Hz, 1H), 8.06 (d, J= 7.9 Hz, 1H), 7.92 (dt, J= 1.7, 7.7 Hz, 1H), 7.49 (ddd, J= 1.0, 4.7, 7.8 Hz, 1H), 6.35 (q, J= 1.4 Hz, 1H), 4.72 (q, J= 6.9 Hz, 2H), 4.56 (t, J= 3.6 Hz, 1H) (m, 1H), (m, 1H), 2.02 (d, J= 0.9 Hz, 3H), (m, 6H). 13 C NMR (75 MHz): δ 159.1, 157.8, 150.2, 138.5, 138.0, 127.0, 124.0, 121.6, 98.8, 65.0, 62.4, 30.4, 25.2, 22.1, (Z)-5: 1 H NMR (300 MHz): δ 8.73 (ddd, J= 0.9, 1.6, 4.7 Hz, 1H), 8.11 (dt, J= 1.0, 7.9 Hz, 1H), 7.93 (dt, J= 1.7, 7.7 Hz, 1H), 7.51 (ddd, J= 1.2, 4.7, 7.6 Hz, 1H), 6.65 (q, J= 1.4 Hz, 1H), 4.62 (t, J= 3.1 Hz, 1H), 4.25 (dd, J= 1.6, 16.6 Hz, 1H), 3.96 (dd, J= S 5
7 1.6, 16.6 Hz, 1H), (m, 1H), (m, 1H), 2.14 (d, J= 1.2 Hz, 3H), (m, 6H). 13 C NMR (75 MHz): δ 159.3, 155.9, 150.2, 137.9, 126.9, 122.1, 121.6, 98.1, 69.7, 62.0, 30.1, 25.1, 18.9, (E)-2,3,3-Trimethyl-1-[(2-pyridyl)sulfonyl)]-1-butene (6). Yellow oil; yield: 0.46 g (60%). 1 H NMR (300 MHz): δ (m, 1H), (m, 1H), 7.93 (dt, J= 1.7, 7.7 Hz, 1H), 7.50 (ddd, J= 1.2, 4.7, 7.8, 1H), 6.40 (d, J= 1.0 Hz, 1H), 2.15 (d, J= 1.0 Hz, 3H), 1.09 (s, 9H). 13 C NMR (75 MHz): δ 167.4, 159.3, 149.9, 137.8, 126.7, 122.1, 121.4, 38.4, 27.9, (E)-4-[(2-Pyridyl)sulfonylmethylene]chroman (7). White solid; mp = ºC; yield: 0.69 g (75%). 1 H NMR (300 MHz): δ 8.71 (ddd, J= 0.9, 1.7, 4.7 Hz, 1H), 8.12 (dt, J= 1.1, 7.9 Hz, 1H), 7.94 (dt, J= 1.6, 7.7 Hz, 1H), (m, 2H), (m, 1H), (m, 3H), 4.26 (t, J= 5.9 Hz, 2H), (m, 2H). 13 C NMR (75 MHz): δ 159.6, 156.9, 150.3, 148.7, 138.1, 132.9, 127.0, 125.1, 121.5, 121.1, 118.9, 118.3, 117.8, 65.2, (E)-1-[(2-Pyridyl)sulfonylmethylene]indan (8). White solid; mp = ºC; yield: 0.63 (73%). 1 H NMR (300 MHz): δ 8.72 (d, J= 4.5 Hz, 1H), 8.15 (d, J= 8.0 Hz, 1H), 7.94 (dt, J= 1.7, 7.9 Hz, 1H), (m, 2H), (m, 2H), (m, 1H), 6.85 (t, J= 2.5 Hz, 1H), (m, 2H), 3.10 (t, J= 6.2 Hz, 2H). 13 C NMR (75 MHz): δ 162.8, 159.6, 150.2, 149.6, 138.3, 137.9, 132.0, 127.0, 126.8, 125.6, 122.2, 121.5, 114.6, 30.4, Typical procedure for the asymmetric conjugate reduction of a,b-unsaturated sulfones: (S)-2-phenyl-1-[(2-pyridyl)sulfonyl)]propane (3a). A solution of CuCl (1.0 mg, 0.01 mmol), tbuona (1.0 mg, 0.01 mmol), (R)-Binap (6.2 mg, 0.01 mmol), PhSiH 3 (100 µl, 0.8 mmol) and (E)-2a (51.8 mg, 0.2 mmol) in toluene (1 ml, 0.2 M) was stirred at room temperature for 24 h. Aqueous saturated NH 4 Cl (20 µl) was added before the mixture was filtered through a short pad of Celite with a thin layer of anhydrous MgSO 4 on the top, and the filtrate was concentrated. The residue was purified by flash cromathography (n-hexane-etoac 4:1) to afford sulfone 3a as a white solid; yield: 49.5 mg (95%); mp = ºC. Analysis by HPLC with chiral stationary phase (Daicel Chiralpak IA, i-proh-hexane 10/90, 0.6 ml/min, t R : 30.3 min for (R)- 20 isomer and 33.3 min for (S)-isomer, 210 nm) showed 94% ee ([α] D = +6 (c 1, CHCl 3 )). 1 H NMR (300 MHz): δ 8.63 (d, J= 4.7 Hz, 1H), 7.84 (d, J= 7.8 Hz, 1H), 7.78 S 6
8 (dt, J= 1.7, 7.7 Hz, 1H), 7.42 (ddd, J= 1.4, 4.7, 7.8 Hz, 1H), (m, 5H), 3.89 (dd, J= 6.2, 13.9 Hz, 1H), (m, 2H), 1.42 (d, J= 6.7 Hz, 3H). 13 C NMR (75 MHz): δ 157.5, 149.9, 143.3, 137.8, 128.4, , 126.7, 122.0, 58.7, 35.0, HRMS (FAB+) Calcd for C 14 H 16 NO 2 S, ; found, (S)-2-(p-Methoxyphenyl)-1-[(2-pyridyl)sulfonyl)]propane (3b). Colorless oil; yield: 92%. [α] 20 D = +7.5 (c 1, CHCl 3 ), 91% ee. HPLC: Daicel Chiralpak IA, i-proh-hexane 10/90, 0.6 ml/min, t R : 35.0 min (R)-isomer and 38.8 min (S)-isomer, 210 nm. 1 H NMR (300 MHz): δ 8.63 (ddd, J= 0.9, 1.5, 4.7 Hz, 1H), (m, 2H), 7.42 (ddd, J= 1.6, 4.7, 7.1 Hz, 1H), 6.99 (d, J= 8.6 Hz, 2H), 6.67 (d, J= 8.6 Hz, 2H), 3.85 (dd, J= 6.8, 14.1 Hz, 1H), 3.73 (s, 3H), (m, 2H), 1.39 (d, J= 6.9 Hz, 3H). 13 C NMR (75 MHz): δ 158.2, 157.6, 149.9, 137.7, 135.4, 127.9, 126.8, 122.0, 113.8, 58.9, 55.2, 34.2, HRMS (FAB+) Calcd for C 15 H 18 NO 3 S, ; found, (S)-2-(p-Nitrophenyl)-1-[(2-pyridyl)sulfonyl)]propane (3c). White solid; yield: 93%; mp = ºC. [α] 20 D = -4.9 (c 1.3, CHCl 3 ), 89% ee. HPLC: Daicel Chiralpak IA, i- PrOH-hexane 20/80, flow rate 0.6 ml/min, t R : 48.1 min (R)-isomer and 50.8 min (S)- isomer, 210 nm. 1 H NMR (300 MHz): δ 8.64 (ddd, J= 0.9, 1.4, 4.7 Hz, 1H), 8.03 (d, J= 8.8 Hz, 2H), 7.87 (dt, J= 1.4, 7.9 Hz, 1H), 7.82 (dt, J= 1.7 and 7.5 Hz, 1H), 7.46 (ddd, J= 1.5, 4.7, 7.4 Hz, 1H), 7.25 (d, J= 8.8 Hz, 2H), (m, 1H), (m, 2H), 1.46 (d, J= 6.8 Hz, 3H). 13 C NMR (75 MHz): δ 157.4, 150.7, 150.0, 146.8, 138.0, 128.0, 127.2, 123.7, 121.8, 57.8, 34.9, HRMS (FAB+) Calcd for C 14 H 15 N 2 O 4 S, ; found, (S)-2-(p-Bromophenyl-1-[(2-pyridyl)sulfonyl)]propane (3d). Colorless oil; yield: 92%. [α] 20 D = +8.5 (c 1.25, CHCl 3 ), 92% ee. HPLC: Daicel Chiralpak IA, i-prohhexane 10/90, 0.6 ml/min, t R : 32.2 min (R)-isomer and 36.8 min (S)-isomer, 210 nm. 1 H NMR (300 MHz): δ (m, 1H), (m, 2H), (m, 1H), 7.24 (d, J= 8.4 Hz, 2H), 6.95 (d, J= 8.4 Hz, 2H), 3.89 (dd, J= 7.5, 14.2 Hz, 1H), (m, 2H), 1.40 (d, J= 6.8 Hz, 3H). 13 C NMR (75 MHz): δ 157.3, 149.9, 142.1, 137.8, 131.4, 128.8, 126.8, 121.9, 120.5, 58.4, 34.6, HRMS (FAB+) Calcd for C 14 H 15 BrNO 3 S, ; found, (S)-1-[(2-Pyridyl)sulfonyl)]-2-[(p-trifluoromethyl)phenyl]propane (3e). Colorless oil; yield: 95%. [α] 20 D = +6.9 (c 1.9, CHCl 3 ), 92% ee. HPLC: Daicel Chiralpak IA, i- PrOH-hexane 10/90, 0.6 ml/min, t R : 27.6 min (R)-isomer and 30.5 min (S)-isomer, 210 nm. 1 H NMR (300 MHz): δ (m, 1H), (m, 2H), (m, 3H), S 7
9 7.17 (d, J= 8.1 Hz, 2H), 3.96 (dd, J= 9.8, 16.3 Hz, 1H), (m, 2H), 1.43 (d, J= 6.8 Hz, 3H). 13 C NMR (75 MHz): δ 157.3, 149.9, 147.0, 137.8, (q, J C-F = 32.5 Hz), 127.5, 127.0, (q, J C-F = 3.8 Hz), 121.9, 58.1, 35.1, HRMS (FAB+) Calcd for C 15 H 15 F 3 NO 2 S, ; found, (S)-2-(o-Methylphenyl)-1-[(2-pyridyl)sulfonyl)]propane (3f). Colourless oil; yield: 93%. [α] 20 D = (c 1, CHCl 3 ), 93% ee. HPLC: Daicel Chiralpak IA, i-prohhexane 10/90, 0.6 ml/min, t R : 23.9 min (R)-isomer and 25.8 min (S)-isomer, 210 nm. 1 H NMR (300 MHz): δ 8.64 (ddd, J= 0.9, 1.5, 4.7 Hz, 1H), (m, 2H), 7.42 (ddd, J= 1.4, 4.7, 7.4 Hz, 1H), (m, 4H), 3.85 (dd, J= 6.4, 14.0 Hz, 1H), 3.75 (sextet, J= 6.6 Hz, 1H), 3.54 (dd, J= 7.1, 14.0 Hz, 1H), 2.30 (s, 3H), 1.39 (d, J= 6.8 Hz, 3H). 13 C NMR (75 MHz): δ 157.6, 149.9, 141.6, 137.8, 135.1, 130.4, 126.9, 126.4, 126.2, 125.6, 121.8, 58.4, 29.8, 21.6, HRMS (FAB+) Calcd for C 15 H 18 NO 2 S, ; found, (S)-2-(o-Bromophenyl-1-[(2-pyridyl)sulfonyl)]propane (3g). Colorless oil; yield: 90%. [α] 20 D = (c 1.6, CHCl 3 ), 94% ee. HPLC: Daicel Chiralpak IA, i-prohhexane 10/90, 0.6 ml/min, t R : 29.9 min (R)-isomer and 33.0 min (S)-isomer, 210 nm. 1 H NMR (300 MHz): δ 8.65 (d, J= 4.6 Hz, 1H), 7.97 (d, J= 7.8 Hz, 1H), 7.84 (dt, J= 1.6, 7.8 Hz, 1H), (m, 2H), (m, 2H), (m, 1H), (m, 2H), (m, 1H), 1.42 (d, J= 6.8 Hz, 3H). 13 C NMR (75 MHz): δ 157.2, 150.0, 142.2, 137.9, 133.0, 128.2, 127.8, 127.7, 127.1, 123.7, 122.1, 57.5, 33.7, HRMS (FAB+) Calcd for C 14 H 15 BrNO 2 S, ; found, (S)-2-(2-Naphtyl)-1-[(2-pyridyl)sulfonyl)]propane (3h). White solid; yield: 89%; mp = ºC. [α] 20 D = (c 0.5, CHCl 3 ), 70% ee. HPLC: Daicel Chiralpak IA, i- PrOH-hexane 10/80, 0.6 ml/min, t R : 28.6 min (R)-isomer and 33.7 min (S)-isomer, 210 nm. 1 H NMR (300 MHz): δ 8.50 (ddd, J= 0.9, 1.6, 4.6 Hz, 1H), (m, 3H), 7.59 (d, J= 8.5 Hz, 1H), (m, 2H), (m, 2H), (m, 2H), (m, 1H), (m, 2H), 1.50 (d, J= 6.8 Hz, 3H). 13 C NMR (75 MHz): δ 157.3, 149.7, 140.3, 137.3, 133.1, 132.2, 128.2, 127.5, 127.4, 126.5, 126.0, 125.8, 125.6, 125.0, 121.9, 58.7, 35.3, HRMS (FAB+) Calcd for C 18 H 18 NO 2 S, ; found, (S)-2-Phenyl-1-[(2-pyridyl)sulfonyl)]butane [(S)-9]. Colorless oil; yield: 92%. [α] D = (c 2, CHCl 3 ), 93% ee. HPLC: Daicel Chiralpak IA, i-proh-hexane 10/90, 0.6 ml/min, t R : 20.8 min (R)-isomer and 22.3 min (S)-isomer, 210 nm. 1 H NMR (300 S 8
10 MHz): δ 8.57 (d, J= 4.5 Hz, 1H), (m, 2H), (m, 1H), (m, 3H), (m, 2H), 3.94 (dd, J= 8.5, 14.6 Hz, 1H), 3.57 (dd, J= 5.6, 14.7 Hz, 1H), (m, 1H), (m, 1H), (m, 1H), 0.76 (t, J= 7.4 Hz, 3H). 13 C NMR (75 MHz): δ 157.5, 149.8, 141.1, 137.6, 128.2, 127.8, 126.7, 126.6, 122.0, 57.5, 42.3, 29.4, HRMS (FAB+) Calcd for C 15 H 18 NO 2 S, ; found, (R)-2-Phenyl-1-[(2-pyridyl)sulfonyl)]butane [(R)-9]. Colorless oil; yield: 92%. [α] D = (c 1.9, CHCl 3 ), 91% ee. HPLC: Daicel Chiralpak IA, i-proh-hexane 10/90, 0.6 ml/min, t R : 20.8 min (R)-isomer and 22.3 min (S)-isomer, 210 nm. 1 H NMR (300 MHz): δ 8.57 (d, J= 4.5 Hz, 1H), (m, 2H), (m, 1H), (m, 3H), (m, 2H), 3.94 (dd, J= 8.5, 14.6 Hz, 1H), 3.57 (dd, J= 5.6, 14.7 Hz, 1H), (m, 1H), (m, 1H), (m, 1H), 0.76 (t, J= 7.4 Hz, 3H). 13 C NMR (75 MHz): δ 157.5, 149.8, 141.1, 137.6, 128.2, 127.8, 126.7, 126.6, 122.0, 57.5, 42.3, 29.4, (2S)-2-Methyl-1-[(2-pyridyl)sulfonyl)]-3-tetrahydropyranoxypropane [(2S)-10]. Colorless oil; yield: 89%. [α] 20 D = (c 1.4, CHCl 3 ), 91% ee. HPLC: Daicel Chiralpak IA, i-proh-hexane 10/90, 0.6 ml/min, t R : 30.1 and 34.4 min (2R)-isomers; 32.3 and 35.8 (2S)-isomers, 210 nm. 1 H NMR (300 MHz): δ 8.76 (d, J= 4.8 Hz, 1H), 8.11 (d, J= 7.9 Hz, 1H), 7.97 (dt, J= 1.6, 7.9 Hz, 1H), 7.55 (dd, J= 4.6, 7.6 Hz, 1H), (m, 1H) (m, 2H), (m, 1H), (m, 1H), 3.38 (dd, J= 4.8, 9.8 Hz, 1H), (m, 1H), (m, 1H), (m, 6H), 1.12 (d, J= 6.7 Hz, 3H). 13 C NMR (75 MHz): δ 157.8, 150.1, 138.1, 127.2, 121.9, 98.9, 98.5, 71.1, 70.4, 62.1, 62.1, 55.0, 54.8, 30.4, 30.3, 29.2, 29.0, 25.3, 19.3, 19.2, 17.1, (2R)-2-Methyl-1-[(2-pyridyl)sulfonyl)]-3-(tetrahydropyranoxy)propane [(2R)-10]. Colorless oil; yield: 91%. [α] 20 D = (c 0.9, CHCl 3 ), 91% ee. HPLC: Daicel Chiralpak IA, i-proh-hexane 10/90, 0.6 ml/min, t R : 30.1 and 34.4 min [for the two (2R)-diastereoisomers]; 32.3 and 35.8 [for the two (2S)-diastereoisomers], 210 nm. 1 H NMR (300 MHz): δ 8.76 (d, J= 4.8 Hz, 1H), 8.11 (d, J= 7.9 Hz, 1H), 7.97 (dt, J= 1.6, 7.9 Hz, 1H), 7.55 (dd, J= 4.6, 7.6 Hz, 1H), (m, 1H) (m, 2H), (m, 1H), (m, 1H), 3.38 (dd, J= 4.8, 9.8 Hz, 1H), (m, 1H), (m, 1H), (m, 6H), 1.12 (d, J= 6.7 Hz, 3H). 13 C NMR (75 MHz): δ 157.8, 150.1, 138.1, 127.2, 121.9, 98.9, 98.5, 71.1, 70.4, 62.1, 62.1, 55.0, 54.8, 30.4, 30.3, 29.2, 29.0, 25.3, 19.3, 19.2, 17.1, S 9
11 (E)-1-[(2-Pyridyl)sulfonyl)]-2,3,3-(trimethyl)butane (11). Yellow oil; yield: 93%. [α] 20 D = (c 2, CHCl 3 ), 91% ee. HPLC: Daicel Chiralpak IA, i-proh-hexane 10/90, 0.6 ml/min, t R : 16.6 min (R)-isomer and 18.8 min (S)-isomer, 210 nm. 1 H NMR (300 MHz): δ 8.75 (d, J= 4.2 Hz, 1H), 8.11 (d, J= 8.2 Hz, 1H), 7.96 (dt, J= 1.5, 7.8 Hz, 1H), 7.54 (dd, J= 5.0, 7.8 Hz, 1H), 3.62 (d, J= 13.9 Hz, 1H), 3.01 (dd, J= 10.0, 14.3 Hz, 1H), (m, 1H), 1.07 (d, J= 6.9 Hz, 3H), 0.83 (s, 9H). 13 C NMR (75 MHz): δ , 150.1, 138.0, 127.2, 122.1, 54.8, 37.6, 33.3, 26.8, HRMS (FAB+) Calcd for C 12 H 20 NO 2 S, ; found, (S)-4-[(2-Pyridyl)sulfonylmethyl]chroman (12). Colorless oil; yield: 93%. [α] 20 D = (c 2, CHCl 3 ), 90% ee. HPLC: Daicel Chiralpak IA, i-proh-hexane 10/90, 0.6 ml/min, t R : 31.2 min (R)-isomer and 35.3 min (S)-isomer, 210 nm. 1 H NMR (300 MHz): δ 8.78 (d, J= 4.7 Hz, 1H), 8.15 (d, J= 7.8 Hz, 1H), 8.00 (dt, J= 1.5, 7.7 Hz, 1H), 7.58 (dd, J= 1.5, 7.7 Hz, 1H), 7.09 (d, J= 7.5 Hz, 2H), (m, 2H), (m, 2H), 3.89 (d, J= 11.8 Hz, 1H), (m, 2H), 2.28 (d, J= 4.8 Hz, 2H). 13 C NMR (75 MHz): δ 157.7, 154.7, 150.2, 138.3, 128.9, 128.4, 127.5, 122.5, 121.9, 120.7, 117.3, 62.5, 57.1, 28.5, HRMS (FAB+) Calcd for C 15 H 16 NO 3 S, ; found, (S)-1-[(2-Pyridyl)sulfonylmethyl]indan (13). Colorless oil; yield: 91%. [α] 20 D = (c 1.9, CHCl 3 ), 90% ee. HPLC: Daicel Chiralpak IA, i-proh-hexane 10/90, flow rate 0.6 ml/min, t R : 34.1 min (R)-isomer and 37.4 min (S)-isomer, 210 nm. 1 H NMR (300 MHz): δ 8.77 (d, J= 4.9 Hz, 1H), 8.16 (d, J= 7.8 Hz, 1H), 7.99 (dt, J= 1.5, 7.6 Hz, 1H), 7.57 (dd, J= 4.6, 7.6 Hz, 1H), (m, 4H), 3.97 (dd, J= 3.0, 14.0 Hz, 1H), (m, 1H), 3.48 (dd, J= 10.2, 14.0 Hz, 1H), (m, 2H), (m, 1H), (m, 1H). 13 C NMR (75 MHz): δ 157.6, 150.2, 143.6, 143.5, 138.2, 127.4, 127.2, 126.5, 124.7, 123.3, 122.0, 56.5, 38.9, 32.3, Protocols for functionalization/desulfonylation (R)-1,3-Diphenylbutane (14). To a solution of sulfone 3a (50 mg, 0.19 mmol, 94% ee) in THF (5 ml), cooled to -78 ºC, was added a 2.5 M solution of n-buli in hexane (84 µl, 0.21 mmol). The resulting orange solution was stirred for 30 min at -78 ºC before it was added benzyl bromide (25 µl, 0.21 mmol). The mixture was stirred at -78 ºC for 2 h, and then aqueous saturated NH 4 Cl (10 ml) was added. The organic layer was S 10
12 separated and the aqueous layer was extracted with EtOAc (2 x 15 ml). The combined organic layers were dried (MgSO 4 ), filtered and concentrated. The residue was dissolved in MeOH (5 ml) and treated with 5 % Na(Hg) (230 mg) and Na 2 HPO 4 (93 mg, 0.6 mmol). The resulting suspension was stirred for 5 h at rt before it was poured into CH 2 Cl 2 (10 ml), filtered and washed with water (2 x 5 ml). The aqueous phase was extracted with CH 2 Cl 2 (3 x 5 ml) and the combined organic phase was dried (MgSO 4 ), filtered and concentrated. The residue was purified by flash chromatography (n-hexane-etoac 100:1), to afford 14 as a colorless oil; yield: 30 mg (75%). [α] 20 D = +9.2 (c 0.7, CHCl 3 ), 94% ee. 1 H NMR (300 MHz): δ (m, 5H), (m, 5H), 2.59 (sextuplet, J= 7.1 Hz, 1H), 2.48 (t, J= 7.9 Hz, 2H), (m, 2H), 1.22 (d, J= 7.1 Hz, 3H). 13 C NMR (75 MHz): δ 139.7, , 128.4, 128.3, , 125.8, 42.5, 41.4, 33.1, HRMS (FAB+) Calcd for C 16 H 19, ; found, Ethyl (R)-3-phenylbutyrate (15). 2 To a solution of sulfone 3a (50 mg, 0.19 mmol, 94% ee) in THF (5 ml), cooled to -78 ºC, was added a 2.5 M solution of n-buli in hexane (84 µl, 0.21 mmol). The resulting orange solution was stirred at -78 ºC for 30 min before ethyl chloroformate (21 µl, 0.21 mmol) was added. The mixture was stirred at -78 ºC for 2 h, and then saturated aqueous NH 4 Cl (10 ml) was added. The organic phase was separated and the aqueous layer was extracted with EtOAc (2 x 10 ml). The combined organic phase was dried (MgSO 4 ), filtered and concentrated. The residue was dissolved in THF (2 ml) and added to a suspension of activated Zn (350 mg) in THF (4 ml) and aqueous saturated NH 4 Cl (4 ml). The mixture was stirred for 12 h at rt before it was filtered through Celite and washed with CH 2 Cl 2 (2 x 10 ml). The combined organic phase was dried (MgSO 4 ), filtered and concentrated. The residue was purified by flash chromatography (n-hexane-etoac 4:1) to afford 15 as a colorless oil; yield: 29.4 mg (80%). [α] 20 D = (c 0.8, CHCl 3 ), 94% ee; [α] Lit D (for the (S)-isomer of 90% ee) = (c 1.1, CHCl 3 ). 1 H NMR (300 MHz): δ (m, 2H), (m, 3H), 4.07 (q, J= 7.1 Hz, 2H), 3.28 (sextet, J= 7.6 Hz, 1H), 2.61 (dd, J= 7.0, 15.0 Hz, 1H), 2.53 (dd, J= 8.0, 15.0 Hz, 1H), 1.31 (d, J= 7.1 Hz, 3H), 1.18 (t, J= 7.1 Hz, 3H). 13 C NMR (75 MHz): δ 172.3, 145.7, 128.4, 126.7, 126.3, 60.2, 42.9, 36.5, 21.7, (S)-isomer: D. H. Appella, Y. Moritani, R. Shintani, E. M. Ferreira, S. L. Buchwald, J. Am. Chem. Soc. 1999, 121, S 11
13 (R)-1,3-Diphenylbutan-1-one (16). 3 To a solution of sulfone 3a (50 mg, 0.19 mmol, 94% ee) in THF (5 ml), cooled to -78 ºC, was added a 2.5 M solution of n-buli in hexane (84 µl, 0.21 mmol). The resulting orange solution was stirred for 30 min at -78 ºC before benzoyl chloride (24 µl, 0.21 mmol) was added. The resulting solution was stirred at -78 ºC for 2 h and then it was added aqueous saturated NH 4 Cl (10 ml). The organic phase was separated and the aqueous phase was extracted with EtOAc (2 x 10 ml). The combined organic phase was dried (MgSO 4 ), filtered and concentrated. The residue was dissolved in THF (2 ml) and added to a suspension of Zn activated (350 mg) in THF (4 ml) and aqueous saturated NH 4 Cl (4 ml). The mixture was stirred for 12 h at rt before it was filtered through Celite and washed with CH 2 Cl 2 (2 x 10 ml). The combined organic phase was dried (MgSO 4 ), filtered and concentrated. The residue was purified by flash chromatography (n-hexane-etoac 3:1), to afford 16 as a white solid; yield: 29.2 mg (69%); mp = ºC. [α] 20 D = (c 0.7, CHCl 3 ), 94% ee; [α] Lit D (for a sample of 82% ee) = (c 1.0, CCl 4 ). HPLC: Daicel Chiralcel OD, i- PrOH-hexane 2/98, 1 ml/min, t R : 17.6 min (S)-isomer and 19.9 min (R)-isomer, 210 nm. 1 H NMR (300 MHz): δ 7.93 (dd, J= 0.9, 8.0 Hz, 2H), (m, 1H), 7.44 (dt, J= 1.8, 8.2 Hz, 2H), (m, 4H), (m, 1H), 3.51 (sextet, J= 7.2 Hz, 1H), 3.31 (dd, J= 5.8, 16.5 Hz, 1H), 3.16 (dd, J= 8.1, 16.2 Hz, 1H), 1.34 (d, J= 6.8 Hz, 3H). 13 C NMR (75 MHz): δ 199.0, 146.5, 132.9, 128.5, 128.2, 128.0, 126.8, 126.2, 47.0, 35.5, (1E,3R)-1,3-diphenyl-1-butene (17). 4 To a solution of sulfone 3a (46 mg, 0.18 mmol, 94% ee) in DME (5 ml), cooled to -78 ºC, was added a 0.5 M solution of KHMDS in toluene (0.72 ml, 0.36 mmol). The resulting orange solution was stirred at -78 ºC for 3 min before benzaldehyde (28 µl, 0.27 mmol) was added. The resulting solution was stirred at -78 ºC for 2 h, and then saturated aqueous NH 4 Cl (10 ml) was added. The organic phase was separated and the aqueous phase was extracted with EtOAc (2 x 10 ml). The combined organic phase was dried (MgSO 4 ), filtered and concentrated. The residue was purified by flash chromatography (n-hexane-etoac 100:1) to afford 17 as a colorless oil; yield: 32.5 mg (87%). [α] 20 D = (c 0.8, CHCl 3 ), 94% ee; [α] Lit D (for a sample of 81% ee) = (c 0.4, CHCl 3 ). HPLC: Daicel Chiralcel OD, i-proh- 3 Y. Kanazawa, Y. Tsuchiya, K. Kobayashi, T. Shiomi, J-i. Itho, M. Kikuchi, Y. Yamamoto, H. Nishiyama, Chem. Eur. J. 2006, 12, P. Mauleón; J. C. Carretero, Org. Lett. 2004, 6, S 12
14 hexane 0.5/99.5, flow rate 0.2 ml/min, t R : 28.4 min (S)-isomer and 30.9 min (R)- isomer, 210 nm. 1 H NMR (300 MHz): δ (m, 10H), 6.44 (d, J= 4.6 Hz, 2H), (m, 1H), 1.50 (d, J= 7.1 Hz, 3H). 13 C NMR (75 MHz): δ 145.6, 137.6, 135.2, 128.5, 128.4, 127.3, 127.0, 126.2, 126.1, 42.5, HRMS (FAB+) Calcd for C 16 H 17, ; found, S 13
15 2. NMR SPECTRA OF NEW COM POUNDS Ph Me 1 SO 2 Ph S 14
16 Ph Me 2a SO 2 (2-Py) S 15
17 MeO Me SO 2 (2-Py) 2b S 16
18 O 2 N Me SO 2 (2-Py) 2c S 17
19 Br Me SO 2 (2-Py) 2d S 18
20 F 3 C Me SO 2 (2-Py) 2e S 19
21 Me SO 2 (2-Py) 2f S 20
22 Br Me 2g SO 2 (2-Py) S 21
23 Me SO 2 (2-Py) 2h S 22
24 Ph Et (E)-4 SO 2 (2-Py) S 23
25 Et Ph SO 2 (2-Py) (Z)-4 S 24
26 SO 2 (2-Py) O O (E)-5 S 25
27 SO 2 (2-Py) O O (Z)-5 S 26
28 SO 2 (2-Py) 6 S 27
29 SO 2 (2-Py) O 7 S 28
30 SO 2 (2-Py) 8 S 29
31 Ph Me SO 2 (2-Py) 3a S 30
32 MeO Me SO 2 (2-Py) 3b S 31
33 O 2 N Me SO 2 (2-Py) 3c S 32
34 Br Me SO 2 (2-Py) 3d S 33
35 F 3 C Me SO 2 (2-Py) 3e S 34
36 Me SO 2 (2-Py) 3f S 35
37 Br Me 3g SO 2 (2-Py) S 36
38 Me 3h SO 2 (2-Py) S 37
39 Et Ph 9 SO 2 (2-Py) S 38
40 SO 2 (2-Py) O O 10 S 39
41 SO 2 (2-Py) 11 S 40
42 SO 2 (2-Py) 12 O S 41
43 SO 2 (2-Py) 13 S 42
44 Ph Ph Me 14 S 43
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,
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. 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
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 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
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
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
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
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
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
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
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
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, *
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
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
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
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
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
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
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
Supporting 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
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 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
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
Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2008
Palladium(0)-catalyzed direct cross-coupling reaction of allylic alcohols with aryland alkenylboronic acids Hirokazu Tsukamoto, Tomomi Uchiyama, Takamichi Suzuki and Yoshinori Kondo Graduate School of
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,
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
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
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,
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
Diastereoselective Access to Trans-2-Substituted Cyclopentylamines
Supporting Information Diastereoselective Access to Trans-2-Substituted Cyclopentylamines Antoine Joosten, Emilie Lambert, Jean-Luc Vasse, Jan Szymoniak jean-luc.vasse@univ-reims.fr jan.szymoniak@univ-reims.fr
Supplementary 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
Crossed Intramolecular Rauhut-Currier-Type Reactions via Dienamine Activation
Crossed Intramolecular Rauhut-Currier-Type Reactions via Dienamine Activation Eugenia Marqués-López, Raquel P. Herrera, Timo Marks, Wiebke C. Jacobs, Daniel Könning, Renata M. de Figueiredo, Mathias Christmann*
SUPPLEMENTARY 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,
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
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,
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
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
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,
Effect of uridine protecting groups on the diastereoselectivity
Supporting Information for Effect of uridine protecting groups on the diastereoselectivity of uridine-derived aldehyde 5 -alkynylation Raja Ben Othman, Mickaël J. Fer, Laurent Le Corre, Sandrine Calvet-Vitale*
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
Supporting 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,
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,
Supporting 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
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,
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,
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
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
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,
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
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
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
Supporting Information. Copyright Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2006
Copyright Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 2006 Silver-Catalyzed Asymmetric Synthesis of 2,3-Dihydrobenzofurans: A New Chiral Synthesis of Pterocarpans Leticia Jiménez-González, Sergio
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,
Chiral 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,
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,
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
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
Supporting Information. for. Angew. Chem. Int. Ed. Z Wiley-VCH 2003
Supporting Information for Angew. Chem. Int. Ed. Z51171 Wiley-VCH 2003 69451 Weinheim, Germany 1 Tin-Free Radical Allylation of B- Alkylcatecholboranes Arnaud-Pierre Schaffner and Philippe Renaud* University
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,
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
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
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
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
Eur. J. Inorg. Chem WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim, 2007 ISSN SUPPORTING INFORMATION
Eur. J. Inorg. Chem. 2007 WILEY-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 2007 ISSN 1434 1948 SUPPORTING INFORMATION Title: Synthesis of Cyclic Carbonates from Atmospheric Pressure Carbon Dioxide Using
Supporting Information
Supporting Information 2017 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim Convenient and General Zinc-Catalyzed Borylation of Aryl Diazonium Salts and Aryltriazenes under Mild Conditions
Supporting 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
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
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
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
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
Supporting Information Palladium-Catalyzed Asymmetric Benzylic Substitution of Secondary Benzyl Carbonates with Nitrogen and Oxygen Nucleophiles Atifah Najib, Koji Hirano,* and Masahiro Miura* Department
Synthesis and evaluation of novel aza-caged Garcinia xanthones
Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry Synthesis and evaluation of novel aza-caged Garcinia xanthones Xiaojin Zhang, a,1 Xiang Li, a,1 Haopeng Sun, * b Zhengyu Jiang,
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
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2015 Supporting information TFA-promoted Direct C H Sulfenylation at the C2 position of non-protected
Total Synthesis of Echinopines A and B
Total Synthesis of Echinopines A and B K. C. Nicolaou,* anfeng Ding, Jean-Alexandre Richard, and David Y.-K. Chen* Contribution from Chemical Synthesis Laboratory@Biopolis, Institute of Chemical and Engineering
Peptidomimetics 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
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
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. Consecutive hydrazino-ugi-azide reactions: synthesis of acylhydrazines bearing 1,5- disubstituted tetrazoles
Supporting Information for Consecutive hydrazino-ugi-azide reactions: synthesis of acylhydrazines bearing 1,5- disubstituted tetrazoles Angélica de Fátima S. Barreto*, Veronica Alves dos Santos, and Carlos
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
Supporting Information Table of Contents 1. General remarks...s1 2. Synthesis of catalyst L S1
Diastereo- and Enantioselective Conjugate Addition of 3-Substituted xindoles to itroolefins Catalyzed by a Chiral i(ac) 2 -Diamine Complex under Mild Conditions Yan-Yan Han,, Zhi-Jun Wu, Wen-Bing Chen,,
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
Supplementary Figure 1. (X-ray structures of 6p and 7f) O N. Br 6p
Supplementary Figure 1 (X-ray structures of 6p and 7f) Me Br 6p 6p Supplementary Figures 2-68 (MR Spectra) Supplementary Figure 2. 1 H MR of the 6a Supplementary Figure 3. 13 C MR of the 6a Supplementary
Supporting Information
Supporting Information Wiley-VCH 2014 69451 Weinheim, Germany Copper-Catalyzed Coupling of Oxime Acetates with Sodium Sulfinates: An Efficient Synthesis of Sulfone Derivatives** Xiaodong Tang, Liangbin
Supplementary Figures
Supplementary Figures Supplementary Figure 1. 1 H NMR spectra for 1-(2-iodopropyl)-3-(trifluoromethyl)benzene Supplementary Figure 2. 13 C NMR spectra for 1-(2-iodopropyl)-3-(trifluoromethyl)benzene Supplementary
Synthesis of eunicellane-type bicycles embedding a 1,3- cyclohexadiene moiety
Supporting Information for Synthesis of eunicellane-type bicycles embedding a 1,3- cyclohexadiene moiety Alex Frichert, 1 Peter G. Jones, 2 and Thomas Lindel*,,1 Address: 1 Institute of Organic Chemistry,
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
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
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
Supplement: 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
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
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. Toward the Total Synthesis of Amphidinolide N: Synthesis of the C8 C29 Fragment
Supporting Information Toward the Total Synthesis of Amphidinolide N: Synthesis of the C8 C29 Fragment Yuki Kawashima, Atsushi Toyoshima, Haruhiko Fuwa, * and Makoto Sasaki * Graduate School of Life Sciences,
Dearomative Indole (3+2) Reactions with Azaoxyallyl Cations New Method for the Synthesis of Pyrroloindolines. Supporting Information
Dearomative Indole (3+2) Reactions with Azaoxyallyl Cations New Method for the Synthesis of Pyrroloindolines Supporting Information Maria C. DiPoto, Russell P. Hughes, and Jimmy Wu* Department of Chemistry,
New Glucuronic Acid Donors for the Modular Synthesis of Heparan Sulfate Oligosaccharides
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 214 Supporting Information New Glucuronic Acid Donors for the Modular Synthesis
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
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
A Cu/Pd Cooperative Catalysis for Enantioselective Allylboration of Alkenes
A Cu/Pd Cooperative Catalysis for Enantioselective Allylboration of Alkenes Tao Jia, Peng Cao, Bing Wang, Yazhou Lou, Xuemei Yin, Min Wang and Jian Liao* Natural Products Research Center, Chengdu Institute
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