Enantioselective Functionalization of Enamides at the β-Carbon Center with Indoles

Angew Chem Int Ed Engl. 2018 Nov 19;57(47):15558-15562. doi: 10.1002/anie.201808764. Epub 2018 Oct 23.

Abstract

We report an enantioconvergent approach for the functionalization of enamides at the β-carbon atom, which involves a chiral Brønsted acid induced tautomerization of 2-amidoallyl into 1-amidoallyl cations. These putative reactive intermediates were produced by ionization of racemic α-hydroxy enamides with a chiral Brønsted acid and captured with substituted indoles in a highly regio- and enantioselective manner.

Keywords: 2-amidoallyl cations; Brønsted acids; asymmetric catalysis; indoles; tautomerization.

Publication types

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

MeSH terms

  • Allyl Compounds / chemistry
  • Amides / chemistry*
  • Carbon / chemistry*
  • Catalysis
  • Cations / chemistry
  • Indoles / chemistry*
  • Stereoisomerism

Substances

  • Allyl Compounds
  • Amides
  • Cations
  • Indoles
  • Carbon