A novel stereoselective route to β-lactams: diastereoselective synthesis of a key intermediate for carbapenem antibiotic (+)-PS-5

Abstract

A combination of stereoselective addition of thiophenol to olefins and subsequent substitution of the corresponding sulfonium group with an O-alkylhydroxamate anion has provided a new practical and stereoselective method for the construction of β-lactams which has been successfully applied to the formal asymmetric synthesis of the carbapenem antibiotic (+)-PS-5 1.