Enantioselective Functionalization of Enamides at the β‐Carbon Center with Indoles. Issue 47 (23rd October 2018)

• Record Type: Journal Article
• Authors: Saputra, Mirza A.; Nepal, Binod; Dange, Nitin S.; Du, Pu; Fronczek, Frank R.; Kumar, Revati; Kartika, Rendy
• Is Part Of: Angewandte Chemie international edition. Volume 57:Issue 47(2018)
• Page Start: 15558
• Page End: 15562
• Publication Date: 2018-10-23
• Subjects: 2-amidoallyl cations -- asymmetric catalysis -- Brønsted acids -- indoles -- tautomerization; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201808764
• Languages: English
• ISSNs: 1433-7851

Abstract

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. Abstract : An enantioconvergent approach for the functionalization of enamides at the β‐carbon atom is enabled by 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.