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

Ilirian Dhimitruka† and John SantaLucia, Jr.*‡
Department of Chemistry, The Ohio State University, 100 W. 18th Avenue, 1042, Columbus, Ohio 43210, and Chemistry Department, Wayne State University, Cass Avenue, Detroit, Michigan 48202
Org. Lett., 2006, 8 (1), pp 47–50
DOI: 10.1021/ol0524048
Publication Date (Web): December 6, 2005
Copyright © 2006 American Chemical Society
†

 The Ohio State University.

,
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

,
‡

 Wayne State University.

, jsl@chem.wayne.edu

Abstract

Abstract Image

A one-pot procedure for the regioselective synthesis of aliphatic esters is described. This was a result of a study on mixed aliphatic−aromatic anhydrides. The data suggest that during the Yamaguchi esterification reaction, a symmetric aliphatic anhydride is produced in situ, which upon reaction with an alcohol yields the ester. We confirmed that benzoyl chloride could be used instead of the sterically hindered Yamaguchi acid chloride. This method was successfully applied in the synthesis of Lux-S aspartic acid inhibitor.

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History

  • Published In Issue January 05, 2006
  • Received October 4, 2005

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