Iridium-catalyzed asymmetric double allylic alkylation of azlactone: efficient access to chiral α-amino acid derivatives

An unprecedented Ir-catalyzed enantioselective double allylic alkylation of less bulky cyclic imine glycinate (azlactone) was rationally designed and developed, providing various bisallylated chiral amino acid derivatives. Control experiments revealed that this transformation proceeds in a sequential manner featuring quasi-dynamic kinetic resolution of the initially-formed monoallylation intermediates.

Automated summary

This article presents an unprecedented enantioselective allylic alkylation method, which was rationally designed and developed to synthesize various chiral amino acid derivatives. Control experiments demonstrated that this transformation proceeds in a sequential manner with quasi-dynamic kinetic resolution of the initially-formed monoallylation intermediates.