Asymmetric Transfer Hydrogenation of gem-Diester-substituted Cyclopropenes Enables the Synthesis of γ-Amino-acid Derivatives and γ-Lactams Bearing Multiple Stereocenters

Abstract

Aryl/alkyl-substituted cyclopropanes and γ-lactams bearing multiple stereocenters are both important molecular skeletons in chemical synthesis and drug discovery. However, a general method that allows access to both types of compounds remains elusive. In this work, through the creative combination of two distinctive research fields-asymmetric transfer hydrogenation and donor-acceptor cyclopropane-we have successfully addressed related challenges in both areas and obtained a variety of trans-cyclopropanes, γ-amino-acid derivatives, and γlactams with excellent enantiomeric excess (ee) values. This work demonstrates the considerable potential of combining conventionally unrelated research domains and may inspire further efforts to solve challenging research problems.