An Efficient Synthesis of (2S) and (2R)-N-Benzoyl-2-t-butyl-4-methyleneoxazolidin-5-one

Abstract

An efficient synthesis of the title compounds in high enantiomeric purity (>98%) involves bromination under photolytic conditions of (2S)- or (2R)-oxazolidinones derived from (S)-alanine followed by treatment of the products with sodium iodide in refluxing acetone. A room-temperature single-crystal X-ray study of (2S,4Z)-N-benzoyl-4-bromomethylene-2-t-butyloxazolidin-5-one is recorded.