Dual catalysis for the redox annulation of nitroalkynes with indoles: enantioselective construction of indolin-3-ones bearing quaternary stereocenters

Angew Chem Int Ed Engl. 2015 Sep 14;54(38):11205-8. doi: 10.1002/anie.201504697. Epub 2015 Aug 5.

Abstract

The enantioselective redox annulation of nitroalkynes with indoles is enabled by gold/chiral phosphoric acid dual catalysis. A range of indolin-3-one derivatives bearing quaternary stereocenters at the C2 position were afforded in good yields and excellent enantioselectivities (up to 96 % ee) from readily available starting materials.

Keywords: asymmetric catalysis; carbenoids; chiral phosphoric acids; gold; indolinones.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkynes / chemistry*
  • Catalysis
  • Indoles / chemistry*
  • Oxidation-Reduction
  • Stereoisomerism

Substances

  • Alkynes
  • Indoles
  • indoline