Pd-catalyzed asymmetric hydrogenation of unprotected indoles activated by Brønsted acids

J Am Chem Soc. 2010 Jul 7;132(26):8909-11. doi: 10.1021/ja103668q.

Abstract

The first highly enantioselective hydrogenation of simple indoles was developed with a Brønsted acid as an activator to form the iminium intermediate in situ, which was hydrogenated using Pd(OCOCF(3))(2)/(R)-H8-BINAP catalyst system with up to 96% ee. The present method provides an efficient route to enantioenriched 2-substituted and 2,3-disubstituted indolines.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Hydrogenation
  • Indoles / chemistry*
  • Palladium / chemistry*
  • Stereoisomerism
  • Substrate Specificity

Substances

  • Indoles
  • Palladium