Alpha-imino esters: versatile substrates for the catalytic, asymmetric synthesis of alpha- and beta-amino acids and beta-lactams

Abstract

The catalytic asymmetric addition of organic nucleophiles to alpha-imino esters has emerged as one of the most promising and intensely investigated routes to optically enriched alpha- and beta-amino acid derivatives and beta-lactams. The importance of alpha-imino esters stems not only from the vast appeal of the potential product classes,(1) but also from their remarkable reactivity as highly electrophilic imines. With each passing year, the number of publications concerning the asymmetric alkylation of imino esters grows significantly. The asymmetric alkylation of imines(2) and N,O-acetals has been in itself a subject of intense interest.(3) In this Account, we wish to illustrate our contribution to this timely field, as well as to highlight the seminal contributions of others.