Synthetic route to chiral indolines via ring-opening/C-N cyclization of activated 2-haloarylaziridines

J Org Chem. 2013 Apr 19;78(8):3867-78. doi: 10.1021/jo400287a. Epub 2013 Apr 11.

Abstract

A practical approach for the synthesis of 3-substituted indolines via regio- and stereoselective SN2-type ring-opening of 2-(2-halophenyl)-N-tosylaziridines with heteroatomic nucleophiles (O, N, and S) followed by palladium-catalyzed intramolecular C-N cyclization is reported in excellent yields (up to >99%) and enantiomeric excess (ee 99%).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aziridines / chemistry*
  • Catalysis
  • Cyclization
  • Hydrocarbons, Halogenated / chemistry*
  • Indoles / chemical synthesis*
  • Indoles / chemistry*
  • Molecular Structure
  • Stereoisomerism

Substances

  • Aziridines
  • Hydrocarbons, Halogenated
  • Indoles
  • indoline