Heteroaryl-Directed Iridium-Catalyzed Enantioselective C–H Alkenylations of Secondary Alcohols
Wenbin Mao, Craig M. Robertson, John F. Bower
Abstract
High Resolution Image Download MS PowerPoint Slide Under iridium-catalyzed conditions, 2-aza-aryl-substituted secondary alcohols undergo C(sp 3 )–H addition reactions to alkynes to provide alkenylated tertiary alcohols. The processes occur with very high regio- and enantioselectivity. An analogous addition to styrene is shown to provide a prototype C(sp 3 )–H alkylation process. A mechanism based on directed aza-enolization of the reactant alcohol is proposed.
Topics & Concepts
ChemistryIridiumEnantioselective synthesisCatalysisAlcoholArylAlkylationKeto–enol tautomerismOrganic chemistryStyreneTertiary alcoholsMedicinal chemistryCombinatorial chemistryAlkylCopolymerPolymerCatalytic C–H Functionalization MethodsAsymmetric Hydrogenation and CatalysisSynthesis and Catalytic Reactions