Asymmetric Allylic C-H Alkylation via Palladium(II)/ cis-ArSOX Catalysis.
Asymmetric Allylic C-H Alkylation via Palladium(II)/ cis-ArSOX Catalysis.
Wei Liu,Siraj M. Ali,Stephen E. Ammann,M. White
TLDR
Pd(II)/ cis-aryl sulfoxide-oxazoline ( cis-ArSOX) catalysts for asymmetric C-H alkylation of terminal olefins with a variety of synthetically versatile nucleophiles are reported, finding use in other transition metal catalyzed processes that operate under oxidative conditions.
Abstract
We report the development of Pd(II)/ cis-aryl sulfoxide-oxazoline ( cis-ArSOX) catalysts for asymmetric C-H alkylation of terminal olefins with a variety of synthetically versatile nucleophiles. The modular, tunable, and oxidatively stable ArSOX scaffold is key to the unprecedented broad scope and high enantioselectivity (37 examples, avg. > 90% ee). Pd(II)/ cis-ArSOX is unique in its ability to effect high reactivity and catalyst-controlled diastereoselectivity on the alkylation of aliphatic olefins. We anticipate that this new chiral ligand class will find use in other transition metal catalyzed processes that operate under oxidative conditions.