The Role of Acyloxyphosphonium Ions and the Stereochemical Influence of Base in the Phosphorane??Mediated Esterification of Alcohols

J McNulty, A Capretta, V Laritchev…

Index: McNulty, James; Capretta, Alfredo; Laritchev, Vladimir; Dyck, Jeff; Robertson, Al J. Angewandte Chemie - International Edition, 2003 , vol. 42, # 34 p. 4051 - 4054

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Citation Number: 39

Abstract

The Mitsunobu reaction [1–4] is widely employed in both condensation and displacement reactions of alcohols with various nucleophiles and normally proceeds with inversion of stereochemistry when chiral secondary alcohols are used. The mechanism of the reaction continues to receive attention and the present view is summarized in Scheme 1. Although the