Exceptional Stereoselectivity in the Synthesis of 1,3,4-Trisubstituted 4-Carboxy β-Lactam Derivatives from Amino Acids

Abstract

[reaction: see text] The base-promoted cyclization of optically pure N-(p-methoxybenzyl)-N-(2-chloro)propionyl amino acid derivatives resulted in a diastereo- and enantioselective approach to valuable 1,3,4,4-tetrasubstituted beta-lactams. The stereochemical outcome of the reaction is exclusively governed by the configuration of the N-(2-chloro)propionyl moiety.