Supporting information for
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- Έρως ŌἈπολλύων Φωτόπουλος
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1 Electronic Supplementary Material (ESI) for Green Chemistry. This journal is The Royal Society of Chemistry 2014 Supporting information for Mesoporous silica KIT-6 supported superparamagnetic CuFe 2 O 4 nanoparticles for catalytic asymmetric hydrosilylation of ketones in air Min Li, Bin Li, Hong-Feng Xia, Danru Ye, Jing Wu* and Yifeng Shi* College of Material, Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou , People s Republic of China Fax : (+86) ; jingwubc@hznu.edu.cn; yfshi@hznu.edu.cn Table of Contents Nitrogen Sorption Isotherms And The Corresponding Pore Size Distribution Curves S2 TGA curve s2 Analytical Data, GC and HPLC Spectra for Chiral Alcohol Products...S3 References......S30 NMR Spectra for Ketones and Alcohol Products......S31 S1
2 a c Volume Adsorbed (cm 3 STP/g) Volume Adsorbed (cm 3 STP/g) dv/dw (cm 3 nm -1 g -1 ) Pore Size (nm) Relative Pressure (P/P 0 ) dv/dw (cm 3 nm -1 g -1 ) Pore Size (nm) Relative Pressure (P/P 0 ) b Volume Adsorbed (cm 3 STP/g) dv/dw (cm 3 nm -1 g -1 ) Pore Size (nm) Relative Pressure (P/P 0 ) Figure S1 Nitrogen sorption isotherms and the corresponding pore size distribution curves of (a) mesoporous silica KIT-6 support, (b) as-made CuFe 2 O sample, (c) and the recycled CuFe 2 O sample after the catalytic reaction. Figure S2 TGA curve of CuFe 2 O catalyst before and after the catalytic reaction under air gas flow with a ramp of 20 o C/min. S2
3 (S)-1-Phenylethanol (2a) 1 OH 1 H NMR (500 MHz, CDCl 3 ): δ (d, J = 6.5 Hz, 3H), 2.01 (s, 1H), 4.91 (q, J = 6.5 Hz, 1H), (m, 5H). 13 C NMR (100 MHz, CDCl 3 ): δ 25.1, 70.4, 125.4, 127.4, 128.5, IR (thin film): ν max (cm 1 ) = 3364, 3030, 1493, 1452, 1007, 761, 699. The conversion and ee value were determined by Capillary GC with a 25m 0.25 mm Chirasil-DEX CB column (Varian, carrier gas, N 2 ); 115 C; isothermal; t R (1a) = 4.62 min; t R (R) = min; t R (S) = min. Chromatograms are illustrated below for a 91% ee sample: S3
4 (S)-1-(2-Methylphenyl)ethanol (2b) 2 Me OH 1 H NMR (400 MHz, CDCl 3 ): δ 1.47 (d, J = 6.4 Hz, 3H), 1.82 (s, 1H), 2.34 (s, 3H), (m, 1H), (m, 3H), 7.52(d, J = 7.2 Hz, 1H). 13 C NMR (100 MHz, CDCl 3 ): δ 18.9, 23.9, 66.8, 124.5, 126.4, 127.2, 130.4, 134.2, IR (thin film): ν max (cm 1 ) = 3357, 3025, 1488, 1460, 1077, 759. The conversion and ee value were determined by Capillary GC with a 25m 0.25 mm Chirasil-DEX CB column (Varian, carrier gas, N 2 ); 125 C; isothermal; t R (1b) = 4.24 min; t R (R) = min; t R (S) = min. Chromatograms are illustrated below for a 79% ee sample: S4
5 (S)-1-(2-Methoxyphenyl)ethanol (2c) 3 OH 1 H NMR (400 MHz, CDCl 3 ): δ 1.49 (d, J = 6.4 Hz, 3H), 2.68 (s, 1H), 3.86 (s, 3H), OMe (m, 1H), (m, 2H), (m, 2H). 13 C NMR (100 MHz, CDCl 3 ): δ 22.9, 55.3, 66.6, 110.4, 120.8, 126.1, 128.3, 133.4, IR (thin film): ν max (cm 1 ) = 3387, 1601, 1492, 1464, 1079, 755. The conversion and ee value were determined by Capillary GC with a 25m 0.25 mm Chirasil-DEX CB column (Varian, carrier gas, N 2 ); 115 C; isothermal; t R (1c) = min; t R (R) = min; t R (S) = min. Chromatograms are illustrated below for a 75% ee sample: S5
6 (S)-1-(2-Chlorophenyl)ethanol (2d) 1,4 Cl OH 1 H NMR (400 MHz, CDCl 3 ): δ 1.50 (d, J = 6.4 Hz, 3H), 2.05 (s, 1H), 5.32 (q, J = 6.4 Hz, 1H), 7.20 (t, J = 7.6 Hz, 1H), (m, 2H), 7.60 (d, J= 7.6 Hz, 1H). 13 C NMR (100 MHz, CDCl 3 ): δ 23.5, 66.9, 126.4, 127.2, 128.4, 129.4, 131.6, IR (thin film): ν max (cm 1 ) = 3357, 3069, 1474, 1437, 1048, 754,692. The conversion and ee value were determined by Capillary GC with a 25m 0.25 mm Chirasil-DEX CB column (Varian, carrier gas, N 2 ); 120 C; isothermal; t R (1d) = 3.95 min; t R (R) = 9.82 min; t R (S) = min. Chromatograms are illustrated below for an 87% ee sample: S6
7 (S)-1-(3-Methylphenyl)ethanol (2e) 3 Me OH 1 H NMR (400 MHz, CDCl 3 ): δ 1.49 (d, J = 6.8 Hz, 3H), 1.88 (s, 1H), 2.36 (s, 3H), 4.86 (q, J = 6.4 Hz, 1H), (m, 1H), (m, 3H). 13 C NMR (100 MHz, CDCl 3 ): δ 21.5, 25.1, 70.5, 122.4, 126.1, 128.2, 138.1, IR (thin film): ν max (cm 1 ) = 3363, 3027, 1489, 1453, 1077, 857, 786, 703. The conversion and ee value were determined by Capillary GC with a 25m 0.25 mm Chirasil-DEX CB column (Varian, carrier gas, N 2 ); 110 C; isothermal; t R (1e) = 8.15 min; t R (R) = min; t R (S) = min. Chromatograms are illustrated below for a 90% ee sample: S7
8 (S)-1-(3-Methoxyphenyl)ethanol (2f) 1,4 OH MeO 1 H NMR (400 MHz, CDCl 3 ): δ 1.49 (d, J = 6.4 Hz, 3H), 2.0 (s, 1H), 3.81 (s, 3H), 4.89 (q, J = 6.4 Hz, 1H), (m, 1H), (m, 2H), (m, 1H). 13 C NMR (100 MHz, CDCl 3 ): δ 25.2, 55.3, 70.4, 110.9, 112.9, 117.7, 129.6, 147.6, IR (thin film): ν max (cm 1 ) = 3386, 1602, 1488, 1456, 1158, 857, 785, 699. The conversion and ee value were determined by Capillary GC with a 25m 0.25 mm Chirasil-DEX CB column (Varian, carrier gas, N 2 ); 130 C; isothermal; t R (1f) = 7.88 min; t R (R) = min; t R (S) = min. Chromatograms are illustrated below for a 96% ee sample: S8
9 (S)-1-(3-Chlorophenyl)ethanol (2g) 1 OH Cl 1 H NMR (400 MHz, CDCl 3 ): δ 1.49 (d, J = 6.4 Hz, 3H), 1.93 (s, 1H), 4.88 (q, J = 6.4 Hz, 1H), (m, 3H), 7.38 (m, 1H). 13 C NMR (100 MHz, CDCl 3 ): δ 25.2, 69.8, 123.6, 125.6, 127.5, 129.8, 134.4, IR (thin film): ν max (cm 1 ) = 3355, 1598, 1574, 1477, 1079, 811, 786, 697. The conversion and ee value were determined by Capillary GC with a 25m 0.25 mm Chirasil-DEX CB column (Varian, carrier gas, N 2 ); 125 C; isothermal; t R (1g) = 7.10 min; t R (R) = min; t R (S) = min. Chromatograms are illustrated below for a 97% ee sample: S9
10 (S)-1-(3-Nitrophenyl)ethanol (2h) 5,6 OH O 2 N 1 H NMR (400 MHz, CDCl 3 ): δ 1.55 (d, J = 6.8 Hz, 3H), 2.05 (s, 1H), 5.03 (q, J = 6.4 Hz, 1H), (m, 1H), 7.72 (d, J = 7.6 Hz, 1H), 8.11 (m, 1H), 8.25 (s, 1H). 13 C NMR (100 MHz, CDCl 3 ): δ 25.5, 69.4, 120.4, 122.4, 129.5, 131.6, 147.9, IR (thin film): ν max (cm 1 ) = 3385, 1531, 1480, 1445, 1069, 875, 809, 739, 689. The conversion and ee value were determined by Capillary GC with a 25m 0.25 mm Chirasil-DEX CB column (Varian, carrier gas, N 2 ); 140 C; isothermal; t R (1h) = min; t R (R) = min; t R (S) = min. Chromatograms are illustrated below for a 91% ee sample: S10
11 (S)-1-(4-Methylphenyl)ethanol thanol (2i) 4 OH 1 H NMR (400 MHz, CDCl 3 ): δ 1.48 (d, J = 6.4 Hz, 3H), 1.91 (s, 1H), 2.35 (s, Me 3H), 4.85 (q, J = 4.8 Hz, 1H), 7.16 (d, J = 7.6 Hz, 2H), 7.26 (d, J = 7.2 Hz, 2H). 13 C NMR (100 MHz, CDCl 3 ): δ 21.1, 25.1, 70.3, 125.4, 129.2, 137.2, IR (thin film): ν max (cm 1 ) = 3364, 1514, 1451, 1089, 817, 728. The conversion and ee value were determined by Capillary GC with a 25m 0.25 mm Chirasil-DEX CB column (Varian, carrier gas, N 2 ); 120 C; isothermal; t R (1i) = 6.58 min; t R (R) = min; t R (S) = min. Chromatograms are illustrated below for a 92% ee sample: S11
12 (S)-1-(4-Fluorophenyl)ethanol (2j) 6,7 OH 1 H NMR (500 MHz, CDCl 3 ): δ1.46 (d, J = 6.4 Hz, 3H), 2.02 (s, 1H), 4.85 (q, F J = 6.4 Hz, 1H), (m, 2H), (m, 2H). 13 C NMR (125 MHz, CDCl 3 ): δ 25.3, 69.8, 115.2, 127.0, 141.5, IR (thin film): ν max (cm 1 ) = 3363, 1605, 1510, 1084, 836. The conversion and ee value were determined by Capillary GC with a 25m 0.25 mm Chirasil-DEX CB column (Varian, carrier gas, N 2 ); 120 C; isothermal; t R (1j) = 5.17 min; t R (R) = 9.61 min; t R (S) = min. Chromatograms are illustrated below for an 89% ee sample: S12
13 (S)-1-(4-Chlorophenyl)ethanol (2k) 1,6 Cl 1089, 829. OH 1 H NMR (400 MHz, CDCl 3 ): δ 1.48 (d, J = 6.4 Hz, 3H), 1.88 (s, 1H), 4.89 (q, J = 6.4 Hz, 1H), (m, 4H). 13 C NMR (100 MHz, CDCl 3 ): δ 25.3, 69.7, 126.8, 128.6, 133.0, IR (thin film): ν max (cm 1 ) = 3356, 1598, 1493, 1452, The conversion and ee value were determined by Capillary GC with a 25m 0.25 mm Chirasil-DEX CB column (Varian, carrier gas, N 2 ); 140 C; isothermal; t R (1k) = 5.17 min; t R (R) = min; t R (S) = min. Chromatograms are illustrated below for a 94% ee sample: S13
14 (S)-1-(4-Bromophenyl)ethanol (2l) 1,6 OH 1 H NMR (400 MHz, CDCl 3 ): δ 1.48 (d, J = 6.8 Hz, 3H), 1.85 (s, 1H), 4.88 (q, Br J = 6.4 Hz, 1H), 7.26 (d, J = 7.6 Hz, 2H), 7.49 (d, J = 8.0 Hz, 2H). 13 C NMR (100 MHz, CDCl 3 ): δ 25.2, 69.8, 121.1, 127.2, 131.5, IR (thin film): ν max (cm 1 ) = 3356, 1593, 1489, 1403, 1086, 824. The conversion and ee value were determined by Capillary GC with a 25m 0.25 mm Chirasil-DEX CB column (Varian, carrier gas, N 2 ); 140 C; isothermal; t R (1l) = 9.02 min; t R (R) = min; t R (S) = min. Chromatograms are illustrated below for a 96% ee sample: S14
15 (S)-1-(4-(Trifluoromethyl)phenyl)ethanol (2m) 1,6 OH 1 H NMR (400 MHz, CDCl 3 ): δ 1.51 (d, J = 6.4 Hz, 3H), 1.92 (s, 1H), 4.98 (q, F 3 C J = 6.4 Hz, 1H), 7.50 (d, J = 8.0 Hz, 3H), 7.62(d, J = 8.0 Hz, 2H). 13 C NMR (100 MHz, CDCl 3 ): δ 25.4, 69.8, 122.8, 125.5, 129.5, IR (thin film): ν max (cm 1 ) = 3356, 1621, 1416, 1126, 842. The conversion and ee value were determined by Capillary GC with a 25m 0.25 mm Chirasil-DEX CB column (Varian, carrier gas, N 2 ); 120 C; isothermal; t R (1m) = 4.94 min; t R (R) = min; t R (S) = min. Chromatograms are illustrated below for a 91% ee sample: S15
16 (S)-1-(4-Nitrophenyl)ethanol (2n) 1,6 OH 1 H NMR (400 MHz, CDCl 3 ): δ 1.52 (d, J = 6.4 Hz, 3H), 2.10 (s, 1H), 5.02 (q, O 2 N J = 6.4 Hz, 1H), 7.54 (d, J = 8.0 Hz, 2H), 8.20 (d, J = 7.6 Hz, 2H). 13 C NMR (100 MHz, CDCl 3 ): δ 25.5, 69.5, 123.7, 126.2, 147.1, IR (thin film): ν max (cm 1 ) = 3383, 2965, 1605, 1519, 1454, 1090, 856, 700. The conversion and ee value were determined by Capillary GC with a 25m 0.25 mm Chirasil-DEX CB column (Varian, carrier gas, N 2 ); 170 C; isothermal; t R (1n) = 7.66 min; t R (R) = min; t R (S) = min. Chromatograms are illustrated below for a 91% ee sample: S16
17 (S)-1-Phenylpropan-1-ol (2o) 4,8 OH 1 H NMR (400 MHz, CDCl 3 ): δ 0.94 (t, J = 7.2 Hz, 3H), (m, 3H), 4.61 (t, J = 6.6 Hz, 1H), (m, 5H). 13 C NMR (100 MHz, CDCl 3 ): δ 10.2, 31.9, 76.0, 126.0, 127.5, 128.4, IR (thin film): ν max (cm 1 ) = 3383, 3063, 2965, 1493, 1454, 1096, 762, 700. The conversion and ee value were determined by Capillary GC with a 25m 0.25 mm Chirasil-DEX CB column (Varian, carrier gas, N 2 ); 95 C; isothermal; t R (1o) = min; t R (R) = min; t R (S) = min. Chromatograms are illustrated below for an 87% ee sample: S17
18 (S)-1-(4-Chlorophenyl)propan-1-ol (2p) 9 OH 1 H NMR (400 MHz, CDCl 3 ): δ 0.90 (t, J = 7.2 Hz, 3H), (m, 2H), Cl 1.96 (br, 1H), 4.56 (m, 1H), (m, 4H). 13 C NMR (100 MHz, CDCl 3 ): δ 10.0, 31.9, 75.3, 127.4, 128.5, 133.1, IR (thin film): ν max (cm 1 ) = 3375, 1598, 1492, 1463, 1091, 825. The conversion was determined by capillary GC with a 30 m 0.25 mm J & W Scientific INNOWAX column; 200 C; isothermal; t R (1p) = 3.04 min; t R (2p) = 4.75 min. The ee value was determined by chiral HPLC analysis with a 25 cm 4.6 mm Daicel Chiralcel OJ-H column (eluent, 2-propanol/hexane 5:95; flow rate: 0.5 ml min 1 ; detection: 254 nm light); t R (S) = min; t R (R) = min. Chromatograms are illustrated below for an 87% ee sample: S18
19 (S)-1,2,3,4-Tetrahydronaphthalen-1-ol (4a) 10 OH 1 H NMR (400 MHz, CDCl 3 ): δ (m, 5H), (m, 2H), 4.78 (t, J = 4.0 Hz, 1H), (m, 3H), (m, 1H). 13 C NMR (100 MHz, CDCl 3 ): δ 18.8, 29.3, 32.3, 68.1, 126.2, 127.6, 128.7, 129.0, 137.1, IR (thin film): ν max (cm 1 ) = 3356, 3020, 1605, 1490, 1455, 1067, 739. The conversion was determined by capillary GC with a 30 m 0.25 mm J & W Scientific INNOWAX column; 200 C; isothermal; t R (3a) = 4.56 min; t R (4a) = 5.41 min. The ee value was determined by chiral HPLC analysis with a 25 cm 4.6 mm Daicel Chiralcel OJ-H column (eluent, 2-propanol/hexane 5:95; flow rate: 1.0 ml min 1 ; detection: 254 nm light); t R (R) = min; t R (S) = min. Chromatograms are illustrated below for a 60% ee sample: S19
20 (S)-1-(Naphthalen-2-yl)ethanol (4b) 1,4 OH 1 H NMR (400 MHz, CDCl 3 ): δ 1.60 (d, J = 6.4 Hz, 3H), 1.98 (s, 1H), (m, 1H), (m, 3H), (m, 4H). 13 C NMR (100 MHz, CDCl 3 ): δ 25.2, 70.5, 123.8, 123.9, 125.8, 126.2, 127.8, 128.0, 128.3, 133.0, 133.4, IR (thin film): ν max (cm 1 ) = 3357, 3055, 1602, 1508, 1449, 1072, 747. The conversion and ee value were determined by Capillary GC with a 25m 0.25 mm Chirasil-DEX CB column (Varian, carrier gas, N 2 ); 130 C; isothermal; t R (3b) = min; t R (R) = min; t R (S) = min. Chromatograms are illustrated below for a 96% ee sample: S20
21 (R)-2-Bromo-1-phenylethanol (4c) 11 OH Br 1 H NMR (400 MHz, CDCl 3 ): δ 2.65 (d, 1H), 3.55 (dd, J = 10.0, 9.2 Hz, 1H), 3.64 (dd, J = 8.0, 2.4 Hz, 1H), (m, 1H), (m, 5H). 13 C NMR (100 MHz, CDCl 3 ): δ 40.2, 73.8, 126.0, 128.5, 128.7, IR (thin film): ν max (cm 1 ) = 3407, 3031, 1493, 1454, 1420, 1061, 764, 701. The conversion and ee value were determined by Capillary GC with a 25m 0.25 mm CP- Cyclodex-β-236 column (Varian, carrier gas, N 2 ); 130 C; isothermal; t R (3c) = min; t R (R) = min; t R (S) = min. Chromatograms are illustrated below for a 91% ee sample: S21
22 (S)-3-Chloro-1-phenylpropan-1-ol (4d) 12 OH Cl 1 H NMR (400 MHz, CDCl 3 ): δ (m, 2H), (br, 1H), (m, 1H), (m, 1H), (m, 1H), (m, 5H). 13 C NMR (100 MHz, CDCl 3 ): δ 41.5, 41.7, 71.3, 125.8, 127.9, 128.7, IR (thin film): ν max (cm 1 ) = 3385, 3031, 1493, 1454, 1054, 765, 701. The conversion was determined by capillary GC with a 30 m 0.25 mm J & W Scientific INNOWAX column; 180 C; isothermal; t R (3d) = 2.74 min; t R (4d) = min. The ee value was determined by chiral HPLC analysis with a 25 cm 4.6 mm Daicel Chiralcel OD column (eluent, 2-propanol/hexane 2:98; flow rate: 1.0 ml min 1 ; detection: 254 nm light); t R (S) = min; t R (R) = min. Chromatograms are illustrated below for an 88% ee sample: S22
23 (R)-4-Chloro-1-phenylbutan-1-ol (4e) 12 OH Cl 1 H NMR (400 MHz, CDCl 3 ): δ (m, 5H), (m, 2H), (m, 1H), (m, 5H). 13 C NMR (100 MHz, CDCl 3 ): δ 29.0, 36.2, 45.0, 73.9, 125.8, 127.8, 128.6, IR (thin film): ν max (cm 1 ) = 3386, 3029, 1493, 1454, 1063, 762, 701. The conversion was determined by capillary GC with a 30 m 0.25 mm J & W Scientific INNOWAX column; 180 C; isothermal; t R (3e) = 3.82 min; t R (4e) = 2.79 min. The ee value was determined by chiral HPLC analysis with a 25 cm 4.6 mm Daicel Chiralcel OD-H column (eluent, 2-propanol/hexane 4:96; flow rate: 0.5 ml min 1 ; detection: 254 nm light); t R (S) = min; t R (R) = min. Chromatograms are illustrated below for an 87% ee sample: S23
24 (R)-(2-Chlorophenyl)(phenyl)methanol (4f) 4,13 Cl OH 1 H NMR (400 MHz, CDCl 3 ): δ 2.37 (s, 1H), 6.23 (d, J = 3.2 Hz, 1H), (m, 8H), (m, 2H). 13 C NMR (125 MHz, CDCl 3 ): δ 72.70, , , , , , , , , , IR (thin film): ν max (cm 1 ) = 3355, 3064, 3031, 1494, 1469, 1441, 752, 699. The conversion was determined by capillary GC with a 30 m 0.25 mm J & W Scientific INNOWAX column; 230 C; isothermal; t R (3f) = 7.69 min; t R (4f) = min. The ee value was determined by chiral HPLC analysis with a 25 cm 4.6 mm Daicel Chiralcel OD-H column (eluent, 2-propanol/hexane 5:95; flow rate: 0.5 ml min 1 ; detection: 254 nm light); t R (R) = min; t R (S) = min. Chromatograms are illustrated below for a 58% ee sample: S24
25 ( )-Cyclohexyl(3,5-dimethoxyphenyl)methanol (4g) 14 OH MeO * OMe 1 H NMR (400 Hz, CDCl 3 ): δ (m, 12H), 3.79 (s, 6H), 4.28 (d, J =6.8 Hz, 1H), (m, 3H). 13 C NMR (100 Hz, CDCl 3 ): δ 160.6, 146.3, 104.6, 99.2, 79.4, 76.8, 55.3, 44.8, 29.4, 28.8, 26.4, 26.1, IR (thin film): ν max (cm 1 ) = 3443, 2927, 1462, 1429, 1064, 697. The conversion was determined by capillary GC with a 30 m 0.25 mm J & W Scientific INNOWAX column; 250 C; isothermal; t R (3g) = 8.06 min; t R (4g) = min. The ee value was determined by chiral HPLC analysis with a 25 cm 4.6 mm Daicel Chiralcel AD column (eluent, 2-propanol/hexane 10:90; flow rate: 1.0 ml min 1 ; detection: 254 nm light); t R (major) = min; t R (minor) = min. [α] 20 D = 5.8 (c = 1, CHCl 3 ). Literature data: 14 [α] 20 D = 5.4 (c = 0.33 in CHCl 3 ) for an ( )-enantiomer sample with the optical value of 92%. Chromatograms are illustrated below for a 95% ee sample: S25
26 ( )-Cyclohexyl[4-(phenyl)phenyl]methanol (4h) 14 OH 1 H NMR (400 Hz, CDCl 3 ): δ (m, 12H), 4.42 (d, J = 6.8Hz, 1H), * (m, 5H), (m, 4H). 13 C NMR (100 Hz, CDCl 3 ): δ 142.7, 140.9, 140.3, 128.8, 127.3, 127.1, 127.1, 127.0, 79.2, 45.0, 29.4, 28.9, 26.5, 26.2, IR (thin film): ν max (cm 1 ) = 3405, 3028, 1486, 1449, 1007, 765, 697. The conversion was determined by capillary GC with a 30 m 0.25 mm J & W Scientific INNOWAX column; 250 C; isothermal; t R (3h) = min; t R (4h) = min. The ee value was determined by chiral HPLC analysis with a 25 cm 4.6 mm Daicel Chiralcel AD column (eluent, 2-propanol/hexane 10:90; flow rate: 1.0 ml min 1 ; detection: 254 nm light); t R (major) = min; t R (minor) = min. [α] D = 17.3 (c = 1.0 in CHCl 3 ). Literature data: 14 [α] 20 D = 19.4 (c = 1.0 in CHCl 3 ) for an ( )-enantiomer sample with the optical value of 95%. Chromatograms are illustrated below for a 90% ee sample: S26
27 (S)-1-(Pyridin-2-yl)ethanol (4i) 15 N OH 1 H NMR (400 MHz, CDCl 3 ): δ 1.51 (d, J = 6.4 Hz, 3H), 1.80 (s, 1H), 4.88 (q, J = 6.4 Hz, 1H), (m, 1H), 7.28 (m, 1H), (m, 1H), 8.52 (d, J =4.8 Hz, 1H) 13 C NMR (100 MHz, CDCl 3 ): δ 24.1, 69.0, 119.8, 122.2, 136.8, 148.1, IR (thin film): ν max (cm 1 ) = 3357, 1596, 1572, 1436, 1083, 787, 752. The conversion was determined by capillary GC with a 30 m 0.25 mm J & W Scientific INNOWAX column; 140 C; isothermal; t R (3i) = 4.06 min; t R (4i) = 7.13 min. The ee value was determined by chiral HPLC analysis with a 25 cm 4.6 mm Daicel Chiralcel OB-H column (eluent, 2-propanol/hexane 10:90; flow rate: 0.5 ml min 1 ; detection: 254 nm light); t R (S) = min; t R (R) = min. Chromatograms are illustrated below for a 64% ee sample: S27
28 (S)-1-(Thiophen-2-yl)ethanol (4j) 15 OH S 1 H NMR (400 MHz, CDCl 3 ): δ 1.60 (d, J = 6.4 Hz, 3H), 2.09 (d, J = 4.0 Hz, 1H), (m, 1H), (m, 2H), (m, 1H). 13 C NMR (100 MHz, CDCl 3 ): δ 25.2, 66.2, 123.2, 124.4, 126.7, IR (thin film): ν max (cm 1 ) = 3363, 1436, 1070, 850, 700. The conversion and ee value were determined by Capillary GC with a 25m 0.25 mm Chirasil-DEX CB column (Varian, carrier gas, N 2 ); 110 C; isothermal; t R (3j) = 8.61 min; t R (R) = min; t R (S) = min. Chromatograms are illustrated below for an 87% ee sample: S28
29 (S)-1-(Thiophen-3-yl)ethanol (4k) 15 OH 1 H NMR (400 MHz, CDCl 3 ): δ 1.52 (d, J = 6.8 Hz, 3H), 1.87 (s, 1H), 4.97 (q, J = 6.8 S Hz, 1H), (m, 1H), (m, 1H), (m, 1H). 13 C NMR (100 MHz, CDCl 3 ): δ 24.5, 66.5, 120.2, 125.7, 126.2, IR (thin film): ν max (cm 1 ) = 3375, 3105, 1453, 1417, 1078, 858, 786. The conversion and ee value were determined by Capillary GC with a 25m 0.25 mm Chirasil-DEX CB column (Varian, carrier gas, N 2 ); 105 C; isothermal; t R (3k) = min; t R (R) = min; t R (S) = min. Chromatograms are illustrated below for an 80% ee sample: S29
30 Referenc 1 T. Ohkuma, M. Koizumi, H. Doucet, T. Pham, M. Kozawa, K. Murata, E. Katayama, T. Yokozawa, T. Ikariya, R. Noyori, J. Am. Chem. Soc., 1998, 120, H. Doucet, T.Ohkuma, K. Murata, T. Yokozawa, M. Kozawa, E. Katayama, A. F. England, T.Ikariya, R. Noyori, Angew. Chem., Int. Ed., 1998, 37, H. Shimizu, D. Igarashi, W. Kuriyama., Y. Yusa, N. Sayo and T. Saito, Org. Lett., 2007, 9, J. Wu, J.-X. Ji, A. S. C. Chan, Proc. Natl. Acad. Sci. U.S.A., 2005, 102, G. Blay, I. Fern andez, V. H. Olmos, A. M. Aleixandre, J. R. Pedro, J. Mol. Catal. A: Chem., 2007, 276, X.-C. Zhang, Y. Wu, F. Yu, F.-F. Wu, J. Wu, A. S. C. Chan, Chem. Eur. J., 2009, 15, N. Mostefai, S. Sirol, J. Courmarcel, O. Riant, Synthesis 2007, B. H. Lipshutz, K. Noson, W. Chrisman, J. Am. Chem. Soc. 2001, 123, M. L. Kantam, J. Yadav, S. Laha, P. Srinivas, B. Sreedhar, F. Figueras, J. Org. Chem. 2009, 74, K. Junge, K Mçller, B. Wendt, S. Das, D. Gçrdes, K. Thurow, M. Beller, Chem. Asian J. 2012, 7, F. Wang, H. Liu, L. Cun, J. Zhu, J. Deng, Y. Jiang, J. Org. Chem. 2005, 70, M. P. Gamble, A. R. C. Smith, M. Wills, J. Org. Chem. 1998, 63, T. Ohkuma, M. Koizumi, M. Yoshida, R. Noyori, Org. Lett. 2000, 2, S.-B. Qi, M. Li, S. Li, J.-N. Zhou, J.-W. Wu, F. Yu, X.-C. Zhang, A. S. C. Chan and J. Wu, Org. Biomol. Chem., 2013, 11, T. Ohkuma, M. Koizumi, M. Yoshida, R. Noyori, Org. Lett. 2000, 2, S30
31 1 H NMR and 13 C NMR Spectra of Alcohols (S)-1-Phenylethanol (2a) S31
32 (S)-1-(2-Methylphenyl)ethanol (2b) S32
33 (S)-1-(2-Methoxyphenyl)ethanol (2c) S33
34 (S)-1-(2-Chlorophenyl)ethanol (2d) S34
35 (S)-1-(3-Methylphenyl)ethanol (2e) S35
36 (S)-1-(3-Methoxyphenyl)ethanol (2f) S36
37 (S)-1-(3-Chlorophenyl)ethanol (2g) S37
38 (S)-1-(3-Nitrophenyl)ethanol (2h) S38
39 (S)-1-(4-Methylphenyl)ethanol thanol (2i) S39
40 (S)-1-(4-Fluorophenyl)ethanol (2j) S40
41 (S)-1-(4-Chlorophenyl)ethanol (2k) S41
42 (S)-1-(4-Bromophenyl)ethanol (2l) S42
43 (S)-1-(4-(Trifluoromethyl)phenyl)ethanol (2m) S43
44 (S)-1-(4-Nitrophenyl)ethanol (2n) S44
45 (S)-1-Phenylpropan-1-ol (2o) S45
46 (S)-1-(4-Chlorophenyl)propan-1-ol (2p) S46
47 (S)-1,2,3,4-Tetrahydronaphthalen-1-ol (4a) S47
48 (S)-1-(Naphthalen-2-yl)ethanol (4b) S48
49 (R)-2-Bromo-1-phenylethanol (4c) S49
50 (S)-3-Chloro-1-phenylpropan-1-ol (4d) S50
51 (R)-4-Chloro-1-phenylbutan-1-ol (4e) S51
52 (R)-(2-Chlorophenyl)(phenyl)methanol (4f) S52
53 ( )-Cyclohexyl(3,5-dimethoxyphenyl)methanol (4g) S53
54 ( )-Cyclohexyl[4-(phenyl)phenyl]methanol (4h) S54
55 (S)-1-(Pyridin-2-yl)ethanol (4i) S55
56 (S)-1-(Thiophen-2-yl)ethanol (4j) S56
57 (S)-1-(Thiophen-3-yl)ethanol (4k) S57
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