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.

• Publication year

  2019

• Venue

  ACS Catalysis

• Publication date

  2019-07-30

• Fields of study

  Chemistry

• Identifiers
  DOI 10.1021/ACSCATAL.9B02523
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar

• No claims are published for this paper.

• No concepts are published for this paper.

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