Bifunctional Iminophosphorane Catalyzed Amide Enolization for Enantioselective Cyclohexadienone Desymmetrization
Charmaine Y. X. Poh, Daniel Rozsar, Jinchao Yang, Kirsten E. Christensen, Darren J. Dixon
Abstract
The organocatalytic enolization of 2-arylacetamides, followed by an enantioselective intramolecular conjugate addition to tethered 2,5-cyclohexadienones, yielding 3D fused N-heterocycles, is described. The transformation represents the first strong activating group-free activation of carboxamides via α-C-H deprotonation in a metal-free, catalytic, and enantioselective reaction, and is achieved by employing a bifunctional iminophosphorane (BIMP) superbase.
Topics & Concepts
DesymmetrizationBifunctionalEnantioselective synthesisKeto–enol tautomerismCatalysisAmideChemistryOrganic chemistryAsymmetric Synthesis and CatalysisAsymmetric Hydrogenation and CatalysisSynthetic Organic Chemistry Methods