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

Abstract

Intimate details of the Mitsunobu mechanism: The trapping of an acyloxytributylphosphonium ion with a chiral secondary alcohol leads to either retention or inversion of stereochemistry in the resulting ester depending on the exclusion or inclusion of a base (see scheme). Insight into the mechanism of phosphorane-mediated esterification processes is presented. Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2003/z51209_s.pdf or from the author. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.