(Thiolan-2-yl)diphenylmethanol Benzyl Ether-Catalyzed Asymmetric Cyclopropanation of Chalcones

J Org Chem. 2023 Jan 6;88(1):559-572. doi: 10.1021/acs.joc.2c02573. Epub 2022 Dec 21.

Abstract

We devised a new method for asymmetric cyclopropanation by employing (S)-(thiolan-2-yl)diphenylmethanol benzyl ether as an organocatalyst. Under optimal conditions, an in situ generated sulfur ylide reacts with (E)-chalcones via a Johnson-Corey-Chaykovsky reaction to afford a variety of cyclopropanes in excellent yields and stereoselectivities. This strategy employs low-environmental-risk reaction conditions and reusable catalysts. Hence, it is a green and efficient method for constructing cyclopropane scaffolds.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Chalcones*
  • Cyclopropanes
  • Ether*
  • Ethers
  • Ethyl Ethers
  • Stereoisomerism

Substances

  • Ether
  • (thiolan-2-yl)diphenylmethanol
  • Chalcones
  • Ethyl Ethers
  • Ethers
  • Cyclopropanes