Asymmetric Ring-Opening of Donor–Acceptor Cyclopropanes with Primary Arylamines Catalyzed by a Chiral Heterobimetallic Catalyst

An
efficient catalytic asymmetric ring-opening reaction of donor–acceptor
cyclopropanes with primary arylamines was developed. The reaction
was achieved through the utilization of a chiral heterobimetallic
catalyst, delivering a variety of chiral γ-amino acid derivatives
in up to 93% yield and 99% ee. Stereochemical experiments
suggest a dominant role for kinetic resolution in this asymmetric
process, which is supported by a computational study of the reaction
coordinate. A class of chiral bimetallic Lewis acid catalysts formed
through a ligand exchange/transmetalation process was introduced in
this work. The symmetric structure of the bimetallic catalyst, i.e.,
Yb­(OTf)3-Yb­[P]3, was confirmed
with X-ray crystallography.