Stereoselective synthesis of 2,3-difunctionalised thioesters using nucleophilic epoxidation of 1-arylthio-1-nitroalkenes

Org Biomol Chem. 2007 Oct 7;5(19):3156-63. doi: 10.1039/b710237b. Epub 2007 Aug 17.

Abstract

Stereoselective nucleophilic epoxidation of protected 3-amino and 3-hydroxy-substituted 1-arylthio-1-nitroalkenes, followed by intramolecular capture involving the amino and hydroxyl protecting groups, has led to the formation of isomeric oxazolidinones 5 and 7, and a cyclic carbonate 11. Together with the oxazolidinone precursor anti-alpha-bromo thioester 15a, the absolute and relative stereochemistry of these compounds has been determined by X-ray crystallography.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemistry*
  • Amino Acids / chemical synthesis*
  • Crystallography, X-Ray
  • Epoxy Compounds / chemistry*
  • Esters / chemical synthesis*
  • Oxazolidinones / chemical synthesis*
  • Stereoisomerism

Substances

  • Alkenes
  • Amino Acids
  • Epoxy Compounds
  • Esters
  • Oxazolidinones