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Asymmetric Allylic C-H Alkylation via Palladium(II)/ cis-ArSOX Catalysis.

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.

SUBMITTER: Liu W

PROVIDER: S-EPMC6370307 | biostudies-literature | 2018 Aug

REPOSITORIES: biostudies-literature

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Asymmetric Allylic C-H Alkylation via Palladium(II)/ cis-ArSOX Catalysis.

Liu Wei W Ali Siraj Z SZ Ammann Stephen E SE White M Christina MC

Journal of the American Chemical Society 20180817 34

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 ol ...[more]

PMID: 30091907

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