Synthesis 2003(14): 2269-2272  
DOI: 10.1055/s-2003-41443
PSP
© Georg Thieme Verlag Stuttgart · New York

Preparation of Chiral N-Vinyl Oxazolidinones by a Simple General Procedure

Catherine Gaulon, Robert Dhal*, Gilles Dujardin
Laboratoire de Synthèse Organique, UCO2M, UMR 6011 CNRS, Université du Maine, 72085, Le Mans,Cedex 9, France
Fax: +33(2)43833902; e-Mail: [email protected];
Further Information

Publication History

Received 22 May 2003
Publication Date:
24 September 2003 (online)

Abstract

A high yielding, general, and practical procedure for the N-vinylation of 2-oxazolidinones via TMSOTf-promoted dehydroalkoxylation of N,O-acetals is described.

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9

Camphorsulfonic acid can be conveniently replaced by p-toluenesulfonic acid.

11

In our hands the N-vinyl oxazolidinones obtained via Hg(II)-catalyzed exchange contained typically (even after distillation or SiO2 chromatography) 10-20% starting material.