K. Nakamura et al. / Tetrahedron: Asymmetry 9 (1998) 4429–4439
4439
3.17. (R)-(+)-4-p-Chlorophenyl-3-butyn-2-ol (R)-4f
Yield 205 mg (80%, 96% ee, pale yellow solid). Mp 65–66°C. [α] 25 37.7 (c 1.0, ether). 200 MHz
D
1
H NMR (CDCl ) δ (ppm) 1.54 (3H, d, J=6.6 Hz), 2.09 (1H, d, J=5.2 Hz), 4.74 (1H, m) and 7.30 (4H,
3
13
m). 50 MHz C NMR (CDCl ) δ (ppm) 134.4, 132.9, 128.6, 121.0, 91.8, 82.9, 58.8 and 24.3. IR (NaCl)
3
−1
ν=3299 and 2230 cm . Anal. calcd for C H OCl: C, 66.49; H, 5.02. Found: C, 66.61; H, 5.02.
10
9
3.18. (R)-(+)-4-p-Nitrophenyl-3-butyn-2-ol (R)-4g
Yield 217 mg (80%, 96% ee, pale yellow solid). Mp 119–120°C. [α]D25 37.5 (c 1.0, ether). 200 MHz
1
H NMR (CDCl ) δ (ppm) 1.56 (3H, d, J=6.8 Hz), 2.12 (1H, s), 4.78 (1H, m), 7.54 (2H, m) and 8.16
3
13
(
(
2H, m). 50 MHz C NMR (CDCl ) δ (ppm) 147.1, 132.4, 129.5, 123.5, 96.2, 82.2, 58.8 and 24.1. IR
3
−1
NaCl) ν=3310 and 2230 cm . Anal. calcd for C H NO : C, 62.82; H, 4.74. Found: C, 62.59; H, 4.78.
10
9
3
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