Z. Wang, J. He and Y. Mu
Journal of Organometallic Chemistry 928 (2020) 121546
(t, J = 7.9 Hz, 1H), 7.02 (t, J = 7.5 Hz, 1H), 6.91 (d, J = 8.2 Hz,
1H), 5.64 (s, 1H), 4.65 (dd, J = 13.1, 3.2 Hz, 1H), 4.58 (dd, J = 13.0,
9.2 Hz, 1H), 3.89 (s, 3H), 3.12 (d, J = 6.1 Hz, 1H) ppm. 13C NMR
(101 MHz, CDCl3, 298 K): δ156.15, 129.96, 127.37, 126.07, 121.33,
110.68, 79.99, 68.00, 55.55 ppm.
4.4.12. (S)-2-nitro-1-(2-nitrophenyl)ethanol (7l)
An enantiomeric excess of 95% ee was determined by HPLC on
a Chiralcel OD-H column. 254 nm, hexane/IPA = 95/5, flow rate:
1 ml·min−1, retention time: 30.36 min (minor), 32.48 min (ma-
jor). 1H NMR (400 MHz, CDCl3, 298 K): δ 8.08 (d, J = 8.2 Hz,
1H), 7.95 (d, J = 7.8 Hz, 1H), 7.75 (t, J = 7.5 Hz, 1H), 7.56 (t,
J = 7.8 Hz, 1H), 6.06 (d, J = 8.7 Hz, 1H), 4.87 (dd, J = 13.8, 1.6 Hz,
1H), 4.56 (dd, J = 13.8, 9.0 Hz, 1H), 3.20 (br s, 1H) ppm. 13C NMR
(101 MHz, CDCl3, 298 K): δ 147.26, 134.54, 134.13, 129.82, 128.82,
125.15, 80.18, 66.90 ppm.
4.4.6. (S)-1-(3-methoxyphenyl)-2-nitroethanol (7f)
An enantiomeric excess of 95% ee was determined by HPLC on
a Chiralcel OD-H column. 254 nm, hexane/IPA = 93/7, flow rate:
1 ml·min−1, retention time: 34.90 min (minor), 50.67 min (ma-
jor). 1H NMR (400 MHz, CDCl3, 298 K): δ 7.34–7.30 (m, 1H), 6.97–
6.96 (m, 2H), 6.91–6.88 (m, 1H), 5.44 (d, J = 9.4 Hz, 1H), 4.60 (dd,
J = 13.4, 9.6 Hz, 1H), 4.51 (dd, J = 13.4, 3.0 Hz, 1H), 3.82 (s, 3H),
2.83 (br s, 1H) ppm. 13C NMR (101 MHz, CDCl3, 298 K): δ 160.21,
139.82, 130.28, 118.18, 114.54, 111.60, 81.33, 71.05, 55.47 ppm.
4.4.13. (S)-2-nitro-1-(4-nitrophenyl)ethanol (7 m)
An enantiomeric excess of 90% ee was determined by HPLC on
a Chiralcel OD-H column. 254 nm, hexane/IPA = 90/10, flow rate:
1 ml·min−1, retention time: 24.18 min (minor), 29.04 min (major).
1H NMR (400 MHz, CDCl3, 298 K): δ 8.26 (d, J = 8.7 Hz, 2H), 7.64
(d, J = 8.7 Hz, 2H), 5.62 (dd, J = 8.1, 4.1 Hz, 1H), 4.61 (dd, J = 12.5,
7.0 Hz, 1H), 4.57 (dd, J = 12.5, 2.8 Hz, 1H), 3.28 (br s, 1H) ppm.
13C NMR (101 MHz, CDCl3, 298 K): δ 148.23, 145.11, 127.08, 124.31,
80.72, 70.09 ppm.
4.4.7. (S)-1-(4-methoxyphenyl)-2-nitroethanol (7 g)
An enantiomeric excess of 91% ee was determined by HPLC on
a Chiralcel OD-H column. 254 nm, hexane/IPA = 93/7, flow rate:
1 ml·min−1, retention time: 29.68 min (minor), 37.60 min (major).
1H NMR (400 MHz, CDCl3, 298 K): δ 7.33 (d, J = 8.5 Hz, 2H), 6.93
(d, J = 8.6 Hz, 2H), 5.42 (d, J = 9.2 Hz, 1H), 4.51 (dd, J = 13.2,
9.6 Hz, 1H), 4.48 (dd, J = 13.2, 3.0 Hz, 1H), 3.82 (s, 3H), 2.70 (br
s, 1H) ppm. 13C NMR (101 MHz, CDCl3, 298 K): δ 160.23, 130.30,
127.43, 114.57, 81.39, 70.83, 55.51 ppm.
4.4.14. (S)-1-(naphthalen-1-yl)-2-nitroethanol (7n)
An enantiomeric excess of 90% ee was determined by HPLC a
Chiralcel OD-H column. 254 nm, hexane/IPA = 90/10, flow rate: 1
ml·min−1, retention time: 19.61 min (minor), 27.74 min (major). 1H
NMR (400 MHz, CDCl3, 298 K): δ 8.03 (d, J = 8.4 Hz, 1H), 7.91 (d,
J = 8.0 Hz, 1H), 7.86 (d, J = 8.2 Hz, 1H), 7.75 (d, J = 7.2 Hz, 1H),
7.61–7.49 (m, 3H), 6.25–6.23 (m, 1H), 4.68 (dd, J = 12.2, 2.5 Hz,
1H), 4.63 (dd, J = 12.2, 7.1 Hz, 1H), 2.99 (s, 1H) ppm. 13C NMR
(101 MHz, CDCl3, 298 K): δ 133.84, 133.67, 129.67, 129.51, 129.42,
127.19, 126.21, 125.62, 123.97, 121.95, 80.89, 68.43 ppm.
4.4.8. (S)-1-(2-chlorophenyl)-2-nitroethanol (7 h)
An enantiomeric excess of 85% ee was determined by HPLC on
a Chiralcel OD-H column. 254 nm, hexane/IPA = 89/1, flow rate:
0.9 ml·min−1, retention time: 69.16 min (minor), 71.38 min (ma-
jor). 1H NMR (400 MHz, CDCl3, 298 K): δ 7.59 (dd, J = 7.6, 1.5 Hz,
1H), 7.32–7.19 (m, 3H), 5.77 (d, J = 9.5 Hz, 1H), 4.60 (dd, J = 13.6,
2.3 Hz, 1H), 4.38 (dd, J = 13.6, 9.6 Hz, 1H), 3.01 (br s, 1H) ppm.
13C NMR (101 MHz, CDCl3, 298 K): δ 135.61, 131.60, 130.06, 129.83,
127.73, 127.63, 79.42, 67.95 ppm.
4.4.15. (S)-1-(naphthalen-2-yl)-2-nitroethanol (7o)
An enantiomeric excess of 88% ee was determined by HPLC on
a Chiralcel OD-H column. 254 nm, hexane/IPA = 87/13, flow rate: 1
ml·min−1, retention time: 32.18 min (minor), 49.12 min (major). 1H
NMR (400 MHz, CDCl3, 298 K): δ 7.81–7.79 (m, 4H), 7.48–7.36 (m,
3H), 5.57–5.52 (m, 1H), 4.65–4.60 (m, 1H), 4.54–4.48 (m, 1H), 2.93
(br s, 1H) ppm. 13C NMR (101 MHz, CDCl3, 298 K): δ 135.55, 133.57,
133.34, 129.15, 128.20, 127.92, 126.85, 126.82, 125.46, 123.33, 81.32,
71.30 ppm.
4.4.9. (S)-1-(4-chlorophenyl)-2-nitroethanol (7i)
An enantiomeric excess of 93% ee was determined by HPLC on
a Chiralcel OD-H column. 254 nm, hexane/IPA = 95/5, flow rate:
1 ml·min−1, retention time: 28.28 min (minor), 33.09 min (major).
1H NMR (400 MHz, CDCl3, 298 K): δ 7.40–7.34 (m, 4H), 5.47–5.45
(m, 1H), 4.58 (dd, J = 13.5, 9.4 Hz, 1H), 4.49 (dd, J = 13.5, 2.9 Hz,
1H), 2.89–2.87 (m, 1H) ppm. 13C NMR (101 MHz, CDCl3, 298 K): δ
136.63, 134.96, 129.35, 127.45, 81.09, 70.42 ppm.
4.4.16. (S)-1-cyclohexyl-2-nitro-ethanol (7p)
An enantiomeric excess of 94% ee was determined by HPLC on a
Chiralcel AD-H column. 254 nm, hexane/IPA = 95/5, flow rate: 0.6
ml·min−1, retention time: 32.46 min (minor), 34.87 min (major).
1H NMR (400 MHz, CDCl3, 298 K): δ 4.49 (dd, J = 13.1, 2.9 Hz,
1H), 4.42 (dd, J = 13.1, 8.9 Hz, 1H), 2.40 (d, J = 5.0 Hz, 1H), 1.85–
1.76 (m, 3H), 1.71–1.65 (m, 2H), 1.52–1.43 (m, 1H), 1.29–1.07 (m,
5H) ppm. 13C NMR (101 MHz, CDCl3, 298 K): δ 79.45, 72.98, 41.58,
28.99, 28.12, 26.25, 26.05, 25.91 ppm.
4.4.10. (S)-1-(2-bromophenyl)-2-nitroethanol (7j)
An enantiomeric excess of 90% ee was determined by HPLC on a
Chiralcel OD-H column. 254 nm, hexane/IPA = 79/1, flow rate: 0.8
ml·min−1, retention time: 78.50 min (minor), 81.22 min (major).
1H NMR (400 MHz, CDCl3, 298 K): δ 7.66 (d, J = 7.7 Hz, 1H), 7.57
(d, J = 8.0 Hz, 1H), 7.40 (t, J = 7.6 Hz, 1H), 7.23 (t, J = 7.6 Hz,
1H), 5.80 (d, J = 9.5 Hz, 1H), 4.69 (dd, J = 13.6, 1.2 Hz, 1H), 4.43
(dd, J = 13.6, 9.7 Hz, 1H), 3.09 (br s, 1H) ppm. 13C NMR (101 MHz,
CDCl3, 298 K): δ 137.17, 133.09, 130.37, 128.31, 127.91, 121.54, 79.46,
70.12 ppm.
4.4.17. (1S,2S)-2-Nitro-1-phenyl-propan-1-ol (8a)
The enantiomeric excess values (92% ee and 67% ee) were de-
termined by HPLC on a Chiralcel AD-H column. 254 nm, hex-
ane/IPA = 90/10, flow rate: 1 ml·min−1, retention time: 8.89 min
(anti, major), 9.96 min (anti, minor), 11.60 min (syn, major),
12.67 min (syn, minor). 1H NMR (400 MHz, CDCl3, 298 K): δ 7.41–
7.36 (m, 5H), 5.41 (t, J = 3.4 Hz, 0.4H, anti), 5.04 (dd, J = 9.2,
3.8 Hz, 0.6H, syn), 4.81–4.74 (m, 0.6H, syn), 4.73–4.67 (m, 0.4H,
anti), 2.63 (s, 0.4H, anti), 2.49 (s, 0.6H, syn), 1.51 (d, J = 6.8 Hz,
1.2H, anti), 1.33 (d, J = 6.8 Hz, 1.8H, syn) ppm. 13C NMR (101 MHz,
CDCl3, 298 K): δ 138.40, 129.38, 129.17, 128.90, 128.69, 127.05,
126.08, 88.53, 87.55, 76.43, 74.01, 16.63, 12.23 ppm.
4.4.11. (S)-1-(4-bromophenyl)-2-nitroethanol (7k)
An enantiomeric excess of 90% ee was determined by HPLC on
a Chiralcel OD-H column. 254 nm, hexane/IPA = 93/7, flow rate:
1 ml·min−1, retention time: 24.14 min (minor), 29.89 min (major).
1H NMR (400 MHz, CDCl3, 298 K): δ 7.53 (d, J = 8.4 Hz, 2H), 7.28
(d, J = 8.4 Hz, 2H), 5.43 (dd, J = 9.6, 2.4 Hz, 1H), 4.57 (dd, J = 13.4,
9.3 Hz, 1H), 4.49 (dd, J = 13.5, 3.1 Hz, 1H), 2.96 (br s, 1H) ppm.
13C NMR (101 MHz, CDCl3, 298 K): δ 137.16, 132.32, 127.75, 123.10,
81.03, 70.47 ppm.
7