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W.-Y. Shen et al.
PAPER
matography (silica gel, EtOAc–hexane, 4:1) to give (S)-4d (116 mg,
94%) as a colorless oil.
1H NMR (400 MHz, CDCl3): d = 0.95 (t, J = 7.2 Hz, 3 H, CH3),
1.29–1.54 (m, 2 H, CH2CH3), 1.74–1.92 (m, 2 H, CHCH2), 2.05 (br,
s, 1 H, OH), 4.92 (t, J = 6.8 Hz, 1 H, CH), 6.94–6.97 (m, 2 H), 7.24
(dd, J = 4.4, 2.0 Hz, 1 H).
1H NMR (400 MHz, CDCl3): d = 1.50 (d, J = 5.6 Hz, 3 H, CH3),
4.21 (br, s, 1 H, OH), 4.91 (q, J = 5.6 Hz, 1 H, CH), 7.26 (dd,
J = 11.2, 6.8 Hz, 1 H), 7.74 (d, J = 6.8 Hz, 1 H), 8.36–8.45 (m, 2 H).
Acknowledgment
(S)-1-(Pyridin-4-yl)ethanol [(S)-4e] and (R)-1-(Pyridin-4-yl)eth-
anol [(R)-4e]4e
We would like to thank the National Natural Science Foundation of
China (No. 20423002; 20703034), Natural Science Foundation of
Fujian Province of China (No. 2008J0235) and State Key Laborato-
ry of Physical Chemistry of Solid Surfaces for financial support.
GC [chiral CP-Chirasil-Dex CB column, 0.25 mm × 25 m; column
temperature = 120 °C (isothermal); inject temperature = 250 °C;
detector temperature = 250 °C; inlet pressure = 0.12 MPa]:
tR = 14.71 (R-isomer), 15.31 min (S-isomer); >99% conversion,
97% ee (S); tR = 3.95 (substrate), 14.85 (R-isomer), 16.97 (S)-iso-
mer), 99% conversion, 96% ee (R). The residue was purified by col-
umn chromatography (silica gel, EtOAc–hexane, 4:1) to give 4e as
a white solid [(S)-4e: 115 mg, 93%; (R)-4e: 116 mg, 94%).
References
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1H NMR (400 MHz, CDCl3): d = 1.50 (d, J = 6.4 Hz, 3 H, CH3),
3.07 (br, s, 1 H, OH), 4.90 (q, J = 6.4 Hz, 1 H, CH), 7.30 (d, J = 4.0
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(S)-1-(5-Methylfuran-2-yl)ethanol [(S)-4f]2d
GC [chiral CP-Chirasil-Dex CB column, 0.25 mm × 25 m; column
temperature = 80 °C (isothermal); inject temperature = 250 °C; de-
tector temperature = 250 °C; inlet pressure = 0.12 MPa]: tR = 7.92
(substrate), 15.00 (R-isomer), 15.29 min (S-isomer); 80% conver-
sion, 82% ee (S). The residue was purified by column chromatogra-
phy (silica gel, EtOAc–hexane, 1:15) to give (S)-4f (90 mg, 71%) as
a colorless oil.
Tetrahedron 1993, 49, 1913. (f) Sablong, R.; Newton, C.;
Dierkes, P.; Osborn, J. A. Tetrahedron Lett. 1996, 37, 4933.
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Morris Watt, W. J. J. Org. Chem. 1998, 63, 7851.
1H NMR (400 MHz, CDCl3): d = 1.52 (d, J = 6.8 Hz, 3 H, CHCH3),
2.00 (s, 1 H OH), 2.28 (s, 3 H, CH3), 4.82 (q, J = 6.8 Hz, 1 H, CH),
5.89 (d, J = 2.4 Hz, 1 H), 6.09 (d, J = 2.4 Hz, 1 H).
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1999, 64, 721.
(R)-1-(5-Chlorothiophen-2-yl)ethanol [(R)-4g]
GC [chiral CP-Chirasil-Dex CB column, 0.25 mm × 25 m; column
temperature = 120 °C (isothermal); inject temperature = 250 °C;
detector temperature = 250 °C; inlet pressure = 0.12 MPa]:
tR = 5.48 (substrate), 13.56 (R-isomer),16.07 (S-isomer); 92% con-
version, 90% ee (R). The residue was purified by column chroma-
tography (silica gel, EtOAc–hexane, 1:15) to give (R)-4g (135 mg,
83%) as a colorless oil.
(2) (a) Kitano, Y.; Kusakabe, M.; Kobayashi, Y.; Sato, F.
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Fogagnolo, M.; Medici, A.; Pedrini, P.; Poli, S.; Gardini, F.
Tetrahedron: Asymmetry 1993, 4, 1607. (e) Fantin, G.;
Fogagnolo, M.; Guerzoni, M. E.; Medici, A.; Pedrini, P.;
Poli, S. J. Org. Chem. 1994, 59, 924. (f) Kaminska, J.;
Gornicka, I.; Sikora, M.; Gora, J. Tetrahedron: Asymmetry
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Kim, J.-S.; Ko, B.-S. Tetrahedron: Asymmetry 1995, 6,
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1H NMR (400 MHz, CDCl3): d = 1.55 (d, J = 6.4 Hz, 3 H, CH3),
2.13 (s, 1 H, OH), 5.01 (q, J = 6.4 Hz, 1 H, CH), 6.72 (d, J = 4.0 Hz,
1 H), 6.76 (d, J = 4.0 Hz, 1 H).
(S)-1-(Thiophen-2-yl)propan-1-ol [(S)-4h]4a
GC [chiral CP-Chirasil-Dex CB column, 0.25 mm × 25 m; column
temperature = 110 °C (isothermal); inject temperature = 250 °C;
detector temperature = 250 °C; inlet pressure = 0.12 MPa]:
tR = 6.81 (substrate), 15.12 (R-isomer), 15.81 min (S-isomer); 90%
conversion, 96% ee (S). The residue was purified by column chro-
matography (silica gel, EtOAc–hexane, 1:15) to give (S)-4h (115
mg, 81%) as a colorless oil.
1H NMR (400 MHz, CDCl3): d = 0.97 (t, J = 7.2 Hz, 3 H, CH3),
1.79–1.96 (m, 2 H, CH2), 2.05 (s, 1 H, OH), 4.84 (t, J = 6.4 Hz, 1 H,
CH), 6.95–6.99 (m, 2 H), 7.24–7.26 (m, 1 H).
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1993, 4, 637. (b) Behnen, W.; Mehler, T.; Martens, J.
Tetrahedron: Asymmetry 1993, 4, 1413. (c) Rijnberg, E.;
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(R)-1-(Thiophen-2-yl)butan-1-ol [(R)-4i]
GC [chiral CP-Chirasil-Dex CB column, 0.25 mm × 25 m; column
temperature = 110 °C (isothermal); inject temperature = 250 °C;
detector temperature = 250 °C; inlet pressure = 0.12 MPa]:
tR = 10.56 (substrate), 24.07 (S-isomer), 24.31 min (R-isomer); 81%
conversion, 97% ee (R). The residue was purified by column chro-
matography (silica gel, EtOAc–hexane, 1:15) to give (R)-4i (106
mg, 68%) as a colorless oil.
Synthesis 2009, No. 14, 2413–2417 © Thieme Stuttgart · New York