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Published on: August 18, 2020
Asymmetric Allylic C-H Alkylation via Palladium(II)/ cis-ArSOX Catalysis
Wei Liu1, Siraj Z Ali1, Stephen E Ammann1
1Roger Adams Laboratory, Department of Chemistry , University of Illinois , Urbana , Illinois 61801 , United States.
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.
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