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Synthesis 2003(14): 2269-2272
DOI: 10.1055/s-2003-41443
DOI: 10.1055/s-2003-41443
PSP
© Georg Thieme Verlag Stuttgart · New YorkPreparation of Chiral N-Vinyl Oxazolidinones by a Simple General Procedure
Further Information
Received
22 May 2003
Publication Date:
24 September 2003 (online)
Publication History
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.
Key words
oxazolidinone - N-vinylation - TMSOTf - N,O-acetal
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References
Camphorsulfonic acid can be conveniently replaced by p-toluenesulfonic acid.
11In our hands the N-vinyl oxazolidinones obtained via Hg(II)-catalyzed exchange contained typically (even after distillation or SiO2 chromatography) 10-20% starting material.