Synthesis of optically active ene carbamates from chromium carbene complexes: use in palladium(II)-assisted synthesis of relays to (+)-thienamycin

Abstract

Attempts to prepare optically active chromium carbene complexes containing the oxazolidinone moiety led instead to an efficient and general synthesis of optically active ene carbamates. One of these has been subjected to palladium(II)-assisted carboacylation, and complete control of stereochemistry was observed. This compound was converted to a key relay to (+)-thienamycin in good chemical and very high optical yield