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

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.

oxazolidinone - N-vinylation - TMSOTf - N,O-acetal

References

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

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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.