Synthesis of both enantiomers of 4-vinyl oxazolidin-2-one from a single precursor: D-isoascorbic acid

Chirality. 2000 Mar;12(3):143-8. doi: 10.1002/(SICI)1520-636X(2000)12:3<143::AID-CHIR7>3.0.CO;2-3.

Abstract

A convenient synthesis of (S)- and (R)-4-vinyl oxazolidin-2-one 1 and 2 from the same inexpensive starting material, D-isoascorbic acid, is described. The title compounds were obtained in 44% and 38% yield, respectively, by operationally simple steps. This approach is a suitable alternative to the literature methods and enhances the synthetic utility of these intermediates. Inc.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Ascorbic Acid*
  • Oxazoles / chemical synthesis*
  • Stereoisomerism

Substances

  • Oxazoles
  • isoascorbic acid
  • Ascorbic Acid