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

Mirza A. Saputra, Louisiana State University
Binod Nepal, Louisiana State University
Nitin S. Dange, Louisiana State University
Pu Du, Louisiana State University
Frank R. Fronczek, Louisiana State University
Revati Kumar, Louisiana State University
Rendy Kartika, Louisiana State University

Abstract

© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim 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.