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Paper | Special issue | Vol 79, No. 1, 2009, pp.821-830
Published online, 2nd December, 2008
DOI: 10.3987/COM-08-S(D)50
The Dakin-West Reaction of N-Acylprolines in the Presence of Inorganic Bases: Unexpected Formation of Enol Esters

Momoko Saeki, Yuri Hagimoto, Hidemitsu Uno, and Masami Kawase*

*Matsuyama University, 4-2 Bunkyo-cho, Matsuyama, Ehime 790-8578, Japan

Abstract

A novel transformation of N-acylprolines (1) to enol esters (2) was realized by utilizing chlorodifluoroacetic or trifluoroacetic anhydrides in the presence of inorganic bases, in which probable intermediates were mesoionic 1,3-oxazolium-5-olates. The structure of the enol ester (2a) was determined by single crystal X-ray analysis.