X.-L. Hou et al. / Tetrahedron: Asymmetry 9 (1998) 1747–1752
1751
3.9. 1-Phenyl-2-phenylaminobenzeneethanol12
1
265 mg, yield: 92%; H NMR (CDCl3/TMS) δ (ppm): 3.10–3.70 (br, 2H), 4.52 (d, J=5.88 Hz,
1H), 4.85 (d, J=5.91 Hz, 1H), 6.55 (d, J=8.58 Hz, 2H), 6.50–6.80 (m, 3H), 7.00–7.40 (m, 10H); mp:
118–120°C (lit:12 mp: 118–120°C); ee: 17.4%; [α]D20=9.4 (c 0.9, CH2Cl2).
3.10. 8-Phenylamino-4-cyclocten-1-ol
1
154 mg, yield: 71%; H NMR (CDCl3/TMS) δ (ppm): 1.05–1.45 (m, 1H), 1.50–1.80 (m, 2H),
1.95–2.15 (m, 2H), 2.20–2.55 (m, 3H), 3.40–3.50 (m, 1H), 3.60–3.70 (m, 1H), 3.70–4.50 (br, 2H),
5.50–5.60 (m, 1H), 5.65–5.80 (m, 1H), 6.70–6.90 (m, 3H), 7.20 (m, 2H); EIMS (relative intensity): 218
(MH+, 77.85), 217 (M+, 100.00), 200 (3.42), 158 (5.58), 119 (45.63), 106 (4.90), 91 (6.09), 77 (7.50),
65 (3.56); IR (KBr): 3315, 3107, 3054, 3027, 2941, 1923, 1690, 1604, 1520, 1498, 1465, 1306, 1256
cm−1; HRMS: C14H19NO calcd: 217.1466; found: 217.1465; mp: 54–55°C; ee: 12.6%; [α]D20=2.1 (c
0.9, CH2Cl2).
3.11. 3-Phenylamino-2-butanol13
1
163 mg, yield: 99%; H NMR (CDCl3/TMS) δ (ppm): 1.15 (d, J=6.47 Hz, 3H), 1.25 (d, J=6.18 Hz,
3H), 2.60–3.30 (br, 2H), 3.30–3.40 (m, 1H), 3.60–3.70 (m, 1H), 6.65–6.85 (m, 3H), 7.20 (t, J=8.29, 7.50
Hz, 2H); ee: 42.7%; [α]D20=−36.2 (c 1.5, CH2Cl2).
Acknowledgements
This work was supported by the National Natural Science Foundation of China (Project 29790127)
and the Chinese Academy of Sciences.
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