Multifaceted interception of 2-chloro-2-oxoacetic anhydrides: a catalytic asymmetric synthesis of β-lactams

Abstract

Aziridine-2-carboxylic acids will react with oxalyl chloride to give morpholin-2,3,5-trionones, cyclic N-carboxyanhydrides or β-lactams depending on the nature of the substituent at the 3-position. All substrates can be diverted to β-lactams upon treatment with a Vilsmeier reagent. The three to four membered ring expansion is stereospecific and proceeds with high yields and diastereoselection. This method provides for an asymmetric synthesis of β-lactams from simple aldehydes via a multi-component catalytic asymmetric aziridination reaction.