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

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.