SYNTHESIS OF THE CHIRAL α,β-UNSATURATED N-ACYL-OXAZOLIDIN-2-ONES BY WITTIG REACTION

Abstract

A new, universal, and versatile method has been developed for the synthesis of the chiral α,β-unsaturated N-acyl-oxazolidin-2-ones 4 based on the Wittig reaction of the triphenylphosphonium salt 7 derived from the (R)-3-(2-Chloro-acetyl)-5,5-dimethyl-4-phenyl-oxazolidin-2-one 6.

Keywords:

• Chiral auxiliaries
• oxazolidin-2-one
• Wittig reaction

The authors are grateful to Guilan University Research Council for financial support of our research program.

Notes

^a All products were analyzed by comparison of their physical and spectroscopic data (¹H NMR, IR) with those of authentic samples.

^b Yields are based on isolated products.