Heteroaryl-Directed Iridium-Catalyzed Enantioselective C-H Alkenylations of Secondary Alcohols

J Am Chem Soc. 2024 Dec 23. doi: 10.1021/jacs.4c16414. Online ahead of print.

Abstract

Under iridium-catalyzed conditions, 2-aza-aryl-substituted secondary alcohols undergo C(sp3)-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(sp3)-H alkylation process. A mechanism based on directed aza-enolization of the reactant alcohol is proposed.