Z. Zeng, G. Zhao, Z. Zhou, C. Tang
FULL PAPER
(S)-(–)-α-Hydroxy-4-methoxyphenylacetonitrile (3d): Colorless oil.
Yield: 147 mg, 90%. [α]2D0 = –38.3 (c = 1.04, CHCl3), 81%ee. 1H
NMR (400 MHz, CDCl3): δ = 2.78 (br. s, 1 H, OH), 3.84 (s, 3 H,
CH3), 5.49 (s, 1 H, CH), 6.96–7.46 (m, 4 Harom) ppm. GC (corre-
sponding acetate, β-DEX120 column): tR = 75.30 (major), 72.97
(minor) min.
Acknowledgments
We are grateful to the National Natural Science Foundation of
China (No. 20472033, 20772058) for generous financial support of
our programs.
(S)-(–)-α-Hydroxy-2-methylphenylacetonitrile (3e): Colorless oil.
Yield: 138 mg, 94%. [α]2D0 = –33.1 (c = 1.10, CHCl3), 80%ee. 1H
NMR (400 MHz, CDCl3): δ = 2.46 (br. s, 3 H, CH3), 5.68 (s, 1 H,
CH), 7.26–7.43 (m, 4 Harom) ppm. GC (corresponding acetate, β-
DEX120 column): tR = 51.16 (major). 50.27 (minor) min.
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(S)-(–)-α-Hydroxy-3-methylphenylacetonitrile (3f): Colorless oil.
Yield: 135 mg, 92%. [α]2D0 = –46.2 (c = 1.17, CHCl3), 88%ee. 1H
NMR (400 MHz, CDCl3): δ = 2.39 (s, 3 H, CH3), 3.30 (br. s, 1 H,
OH), 5.47 (s, 1 H, CH), 7.23–7.33 (m, 4 Harom) ppm. GC (corre-
sponding acetate, β-DEX120 column): tR = 53.70 (major), 51.30
(minor) min.
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(S)-(–)-α-Hydroxy-4-methylphenylacetonitrile (3g): Colorless oil.
Yield: 132 mg, 90%. [α]2D0 = –47.9 (c = 1.02, CHCl3), 92%ee. 1H
NMR (400 MHz, CDCl3): δ = 1.98 (s, 3 H, CH3), 3.10 (br. s, 1 H,
OH), 5.50 (s, 1 H, CH), 7.25–7.42 (m, 4 Harom) ppm. GC (corre-
sponding acetate, β-DEX120 column): tR = 56.64 (major), 53.58
(minor) min.
(S)-(–)-2-Hydroy-2-(1-naphthyl)acetonitrile (3h): Colorless oil.
Yield: 156 mg, 85%. [α]2D0 = –49.8 (c = 1.00, CHCl3), 76%ee. 1H
NMR (300 MHz, CDCl3): δ = 3.43 (d, J = 6.9 Hz, 1 H, OH), 6.17
(d, J = 6.9 Hz, 1 H, CH), 7.42–8.22 (m, 7 Harom) ppm. GC (corre-
sponding acetate, β-DEX120 column): tR = 155.49 (major), 151.58
(minor) min.
(R)-(–)-2-(Furan-2-yl)-2-hydroxyacetonitrile (3i): Colorless oil.
Yield: 111 mg, 90%. [α]2D0 = –36.1 (c = 1.07, CHCl3), 83%ee. 1H
NMR (400 MHz, CDCl3): δ = 4.31 (br. s, 1 H, OH), 5.57 (s, 1 H,
CH), 7.27–7.71 (m, 3 Harom) ppm. GC (corresponding acetate, β-
DEX120 column): tR = 26.13 (major), 28.53 (minor) min.
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(S)-(–)-(E)-2-Hydroxy-4-phenylbut-3-enenitrile (3j): Colorless oil.
Yield: 142 mg, 89%. [α]2D0 = –20.9 (c = 1.03, CHCl3), 78%ee. 1H
NMR (300 MHz, CDCl3): δ = 2.82 (br. s, 1 H, OH), 5.17 (d, J =
4.8 Hz, 1 H, CH), 6.24–6.29 (dd, J = 6.0, 15.6 Hz, 1 H, PhC=CH),
6.92 (d, J = 15.6 Hz, 1 H, PhHC=C), 7.31–7.38 (m, 3 Harom), 7.41–
7.43 (m, 2 Harom) ppm. GC (corresponding acetate, β-DEX120 col-
umn): tR = 77.19 (major), 75.36 (minor) min.
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(R)-(–)-2-Hydroxy-4-phenylbutanenitrile (3k): Colorless oil. Yield:
143 mg, 89%. [α]2D0 = –4.8 (c = 1.07, CHCl3), 42%ee. 1H NMR
(300 MHz, CDCl3): δ = 2.15–2.21 (m, 2 H, CH2), 2.61 (br. s, 1 H,
OH), 2.83–2.88 (m, 2 H, CH2), 4.43 (t, J = 6.9 Hz, 1 H, CH), 7.21–
7.24 (m, 3 Harom), 7.30–7.34 (m, 2 Harom) ppm. GC (corresponding
acetate, β-DEX120 column): tR = 67.38 (major), 65.59 (minor) min.
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Supporting Information (see footnote on the first page of this arti-
cle): NMR spectra of the ligand and catalyst, GC spectra of the
prepared cyanohydrin acetates.
Received: December 7, 2007
Published Online: February 11, 2008
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