Tetrahedron: Asymmetry

Stereochemical consequences of the use of chiral N-phosphoryl oxazolidinones in the attempted kinetic resolution of bromomagnesium alkoxides

S Jones, D Selitsianos

Index: Jones, Simon; Selitsianos, Dimitrios Tetrahedron Asymmetry, 2005 , vol. 16, # 18 p. 3128 - 3138

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Citation Number: 9

Abstract

A number of chiral N-phosphoryl oxazolidinones have been prepared and evaluated as asymmetric phosphoryl transfer agents with the magnesium alkoxide of 1-phenyl ethanol. The reaction proceeded with little stereoselection, which was shown to be a consequence of the reaction mechanism that occurs with inversion of configuration at phosphorus consistent with in-line attack opposite the leaving group.