First resolution of ( R, R)- and ( S, S)-bis(1-hydroxyphenylmethyl)phosphinic acids via diastereomeric salt formation with enantiopure 1-phenylethylamines

Babak Kaboudin,Hamideh Haghighat,Tsutomu Yokomatsu

doi:10.1016/j.tetasy.2008.03.004

First resolution of ( R, R)- and ( S, S)-bis(1-hydroxyphenylmethyl)phosphinic acids via diastereomeric salt formation with enantiopure 1-phenylethylamines

Babak Kaboudin, Hamideh Haghighat + Show 1 more

https://doi.org/10.1016/j.tetasy.2008.03.004

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Journal: Tetrahedron: Asymmetry	Publication Date: Mar 28, 2008
Citations: 17

Affiliation: Institute for Advanced Studies in Basic Sciences, Tokyo University of Pharmacy and Life Sciences

#Phosphinic Acid #Diastereomeric Salt Formation + Show 7 more

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Abstract

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-hydroxyphenylmethyl)phosphinic acid with ( R)-2-phenylethylamine gave access to ( S, S)-bis(1-hydroxyphenylmethyl)phosphinic acid in good yield.

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