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Investigation of the Yamaguchi Esterification Mechanism. Synthesis of a Lux-S Enzyme Inhibitor Using an Improved Esterification Method

Ilirian Dhimitruka and John SantaLucia, Jr.*

*Chemistry Department, Wayne State University, Cass Avenue, Detroit, Michigan 48202, Email: jslchem.wayne.edu

I. Dhimitruka, J. SantaLucia, Org. Lett., 2006, 8, 47-50.

DOI: 10.1021/ol0524048 (free Supporting Information)


Abstract

The data of a study on mixed aliphatic-aromatic anhydrides suggest that during the Yamaguchi esterification reaction, a symmetric aliphatic anhydride is produced in situ, which upon reaction with an alcohol yields the ester. A one-pot procedure for the regioselective synthesis of aliphatic esters is described using benzoyl or p-toluoyl chloride instead of the sterically hindered Yamaguchi acid chloride.

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proposed mechanism



Key Words

Yamaguchi Esterification, Esterifications


ID: J54-Y2006-150