Highly enantioselective construction of the key azetidin-2-ones for the synthesis of carbapenem antibiotics via intramolecular C–H insertion reactions of α-methoxycarbonyl-α-diazoacetamides catalysed by chiral dirhodium() carboxylates

Abstract

A highly enantioselective construction of 3-oxa-1-azabicyclo[4.2.0]octanes (up to 96% ee) has been achieved by intramolecular C–H insertion of α-methoxycarbonyl-α-diazoacetamides catalysed by dirhodium(II) complexes incorporating N-phthaloyl-(S)-amino acids as chiral bridging ligands, which provides a new, catalytic asymmetric route to key intermediates for carbapenem antibiotics.