Appl Microbiol Biotechnol
min, 254 nm): tr (S)-benzoin 14.7 min, tr (R)-benzoin
21.6 min).
13C-NMR (75 MHz, CDCl3): δ 145.0, 128.4, 127.5, 125.9,
74.4, 41.2, 19.0, 13.9 ppm.
Diphenylmethanol (2b)
The enantiomeric excess (ee %) was determined by HPLC
using Chiralcel OD column (n-hexane/i-PrOH 99:1, 0.5 mL/
min, 254 nm): tr (R)-1-phenylbutanol 19.4 min, tr (S)-1-
phenylpbutanol 23.2 min.
1H-NMR (300 MHz, CDCl3): δ 2.19 (d, J=4.0 Hz, 1H),
5.86 (d, J=4.0 Hz, 1H), 7.25–7.28, (m, 2H), 7.32–7.35 (m,
4H), 7.38–7.40 (m, 4H) ppm.
13C-NMR (75 MHz, CDCl3): δ 143.8 128.5, 127.6, 126.5,
76.2 ppm.
The molar conversion was determined by HPLC using
LichroCART 250–4,6 MeOH/H2O 65:35, 0.7 mL/min,
220 nm: tr diphenylmethanol 12.5 min, tr benzophenone
20.6 min.
1-Pyridin-3yl-ethanol (2i)
[α]D25=−38.04° (c 0.4 ethanol) lit.4 [α]D20=−39.0° (c 0.93
ethanol).
1H-NMR (300 MHz, CDCl3): δ 8.46–8.33 (m, 2H), 7.75–
7.70 (m, 1H), 7.24 (dd, J1=8.0 Hz, J2=5.0 Hz, 1H), 4.90 (q,
J=6.5 Hz, 1H), 4.5 (br s, 1H, OH), 1.49 (d, J=6.5 Hz, 3H)
ppm.
Ethyl mandelate (2d)
[α]D25=+88.7° (c 0.7 EtOH ) lit.2 [α]D22=+97.33° (c 1.1
EtOH).
13C-NMR (75 MHz, CDCl3): δ 148.0, 147.0, 141.8, 133.5,
123.5, 67.5 25.1 ppm.
1H-NMR (300 MHz, CDCl3): δ 7.35–7.42 (m, 5H), 5.15 (s,
1H), 4.15–4.25 (m, 2H), 1.20 (m, 3H) ppm.
13C-NMR (75 MHz, CDCl3): δ 173.7, 138.5, 128.7, 128.5,
126.6, 73.0, 62.3, 14.2 ppm.
The enantiomeric excess (ee %) was determined by HPLC
using Phenomenex Lux cellulose 2 column (n-hexane/i-PrOH
90:10, 0.7 mL/min, 254 nm): tr (R)-(1-pyridin-3yl)ethanol
20.46 min, tr (S)-(1-pyridin-3yl)ethanol 25.30 min.
1-Pyridin-3yl-propanol (2j)
The enantiomeric excess (ee %) was determined by HPLC
using Chiralcel OD-H column (n-hexane/i-PrOH 90:10,
1.0 mL/min, 210 nm): tr (S)-ethyl mandelate 6.0 min, tr (R)-
ethyl mandelate 10.0 min).
[α]D25=−40.0° (c 0.2 methanol) lit.6 [α]D20=−41.4° (c 2.1
methanol).
1H-NMR (300 MHz, CDCl3): δ 8.31 (m, 1H), 8.25 (m,
1 H), 7.63 (m, 1 H), 7.15 (m, 1 H), 4.90 (s, 1 H), 4.51 (t, J=
6.6 Hz, 1 H), 1.68 (m, 2 H), 0.82 (t, J=7.41 Hz, 3 H) ppm.
13C-NMR (75 MHz, CDCl3,): δ 147.9, 147.4, 140.6, 133.9,
123.3, 72.8, 31.9, 9.8 ppm.
1-Phenylethanol (2e)
[α]D25=+40.0° (c 0.5 chloroform) lit.3 [α]D25=+36.0° (c
1.0 chloroform).
1H-NMR (300 MHz, CDCl3): δ 7.20–7.35 (m, 5H), 4.85
(q, J=6.4 Hz, 1H), 1.46 (d, J=6.4 Hz, 3H) ppm. 13C-NMR
(75 MHz, CDCl3): δ 145.9, 128.5, 127.5, 125.4, 70.4,
25.2 ppm.
The enantiomeric excess (ee %) was determined by
HPLC using Phenomenex Lux cellulose 2 column (n-
hexane/i-PrOH 90:10, 0.7 mL/min, 254 nm): tr (R)-(1-
pyridin-3yl)propanol 18.2 min, tr (S)-(1-pyridin-
3yl)propanol 21.1 min.
The enantiomeric excess (ee %) was determined by HPLC
using Chiralcel OD column (n-hexane/i-PrOH 95:5, 0.7 mL/
min, 254 nm): tr (R)-1-phenylethanol 14.2 min, tr (S)-1-
phenylethanol 18.0 min.
(1-Thiophen-2-yl)ethanol (2k)
[α]D25=−20.80° (c 0.2 chloroform) lit.4 [α]D20=−23.2° (c
0.79 chloroform).
1-Phenylpropanol (2f)
[α]D25=+20.5° (c 0.2 chloroform) lit.4 [α]D20=+22.2° (c
1.0 chloroform).
1H-NMR (300 MHz, CDCl3): δ 7.25–7.18 (m, 1H), 6.95–
6.92 (m, 2H), 5.07 (q, J=6.5 Hz, 1H), 2.54 (br s, 1H, OH),
1.56 (d, J=6.5 Hz, 3H) ppm.
1H-NMR (300 MHz, CDCl3): δ 7.35–7.22 (m, 5H), 4.54 (t,
J=6.5 Hz, 3H), 2.20 (br s, 1H, OH), 1.83–1.68 (m, 2H), 0.89
(t, J=7.5 Hz, 3H) ppm.
13C-NMR (75 MHz, CDCl3): δ 150.0, 126.6, 124.4, 123.2,
66.2, 25.2 ppm.
13C-NMR (75 MHz, CDCl3): δ 144.6, 128.4, 127.5, 126.0,
76.0, 31.9, 10.1 ppm.
The enantiomeric excess (ee %) was determined by HPLC
using Phenomenex Lux cellulose 3 column (n-hexane/i-PrOH
90:10, 0.5 mL/min, 254 nm): tr (S)-(1-thiophen-2-yl)ethanol
13.5 min, tr (R)-(1-thiophen-2-yl)ethanol 15.90 min.
(1-Furan-2-yl)ethanol (2l)
The enantiomeric excess (ee %) was determined by HPLC
using Chiralcel OD-H column (n-hexane/i-PrOH 98:2,
1.0 mL/min, 254 nm): tr (R)-1-phenylpropanol 16.5 min, tr
(S)-1-phenylpropanol 19.5 min.
[α]D25=−20.5° (c 0.2 chloroform) lit.4 [α]D20=−13.6° (c
0.55 chloroform).
1-Phenylbutanol (2g)
[α]D25=−40.5° (c 0.2 chloroform) lit.7 [α]D25=−43.5° (c
1.0 chloroform).
1H-NMR (400 MHz, CDCl3): δ 7.36 (dd, J1=2.0 HzJ2=
1.0 Hz, 1H,), 6.32 (dd, J1=3.0 HzJ2=2.0 Hz, 1H,), 6.22 (d,
J=3.0 Hz, 1H,), 4.86 (q, J=6.5 Hz, 1H,), 2.35 (br s, 1H, OH),
1.52 (d, J=6.5 Hz, 3H,) ppm.
1H-NMR (300 MHz, CDCl3): δ 7.34–7.32 (m, 4H), 7.27–
7.24 (m, 1H), 4.66 (t, J=6.5 Hz, 1H), 1.93 (br s, 1H, OH),
1.80–1.63 (m, 2H), 1.46–1.27 (m, 2H), 0.92 (t, J=7.5 Hz, 3H)
ppm.
13C NMR (100 MHz, CDCl3): δ 157.7, 141.8, 110.1,
105.1, 63.6, 21.2 ppm.