Tetrahedron: Asymmetry

Chiral, non-racemic α-hydroxyphosphonates and phosphonic acids via stereoselective hydroxylation of diallyl benzylphosphonates

D Skropeta, RR Schmidt

Index: Skropeta, Danielle; Schmidt, Richard R. Tetrahedron Asymmetry, 2003 , vol. 14, # 2 p. 265 - 273

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Citation Number: 54

Abstract

Chiral, non-racemic α-hydroxyphosphonates have been prepared in high enantiomeric excess (96–98% ee), via stereoselective oxaziridine-mediated hydroxylation of diallyl benzylphosphonates. The enantiomeric purity and absolute configuration of the α- hydroxyphosphonates was established from 1H and 31P NMR spectroscopy of the (S)-O- methylmandelate esters. Deprotection of the diallyl α-hydroxyphosphonates under neutral ...