An Organocatalytic Kinetic Resolution of Aziridines by Thiol Nucleophiles

Org Lett. 2021 Jan 15;23(2):554-558. doi: 10.1021/acs.orglett.0c04074. Epub 2020 Dec 31.

Abstract

We report the first organocatalytic kinetic resolution of unactivated aziridines by sulfur nucleophiles with excellent enantioselectivity. A suitable chiral phosphoric acid was found to catalyze the intermolecular ring opening under mild conditions, furnishing a range of highly enantioenriched β-amino thioethers and aziridines, both of which are useful synthetic building blocks.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aziridines / chemistry*
  • Catalysis
  • Kinetics
  • Molecular Structure
  • Phosphoric Acids / chemistry*
  • Sulfhydryl Compounds / chemistry*

Substances

  • Aziridines
  • Phosphoric Acids
  • Sulfhydryl Compounds
  • phosphoric acid