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

Organic & Biomolecular Chemistry Pub Date: 2007-08-17 DOI: 10.1039/B710237B

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-α-bromo thioester 15a, the absolute and relative stereochemistry of these compounds has been determined by X-ray crystallography.

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