First resolution of (R,R)- and (S,S)-bis(1-hydroxyphenylmethyl)phosphinic acids via diastereomeric salt formation with enantiopure 1-phenylethylamines
作者:Babak Kaboudin、Hamideh Haghighat、Tsutomu Yokomatsu
DOI:10.1016/j.tetasy.2008.03.004
日期:2008.4
The resolution of racemic bis(1-hydroxyphenylmethyl)phosphinic acid with enantiopure 1-phenylethylamines via diastereomeric salt formation was investigated. X-ray crystallographic analysis of the salt clearly revealed that (S)-1-phenylethylamine was an efficient resolving agent for obtaining the single enantiomer (R,R)-bis(1-hydroxyphenylmethyl)phosphinic acid. Resolving racemic bis(1-hydroxvphenylmethyl)phosphinic acid with (R)-2-phenylethylamine gave access to (S,S)-bis(1-hydroxyphenylmethyl)phosphinic acid in good yield. (C) 2008 Elsevier Ltd. All rights reserved.