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Conformation of ( RS )‐ and ( SS )‐ O , O ‐(2,2′‐Binaphthyl)‐ N ‐(α‐benzylethyl) Phosphamidate
Author(s) -
Liu Jun,
Wang Min,
Wang Mingan,
Chen Wanyi,
Shen Qifeng,
Ma Libin
Publication year - 1997
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/(sici)1097-458x(199702)35:2<79::aid-omr33>3.0.co;2-5
Subject(s) - chemistry , diastereomer , molecular mechanics , stereochemistry , crystallography , crystal structure , diffraction , molecule , computational chemistry , organic chemistry , optics , physics
The conformations of ( RS )‐ and ( SS )‐ O , O ‐(2,2′‐binaphthyl)‐ N ‐(α‐benzylethyl) phosphamidate (binaphthol phosphamidate) were examined by means of NMR, single‐crystal x‐ray diffraction and molecular mechanics calculations. There are physical and chemical differences between the two diastereoisomers such as different abilities to form clathrates with ethanol. These differences provide the theoretical basis for the resolution of racemic binaphthol with optically active α‐phenylethylamine. © 1997 by John Wiley & Sons, Ltd.