Efficient Synthesis of Sulfur-Stereogenic Sulfoximines via Ru(II)-Catalyzed Enantioselective C–H Functionalization Enabled by Chiral Carboxylic Acid

Efficient Synthesis of Sulfur-Stereogenic Sulfoximines via Ru(II)-Catalyzed Enantioselective C–H Functionalization Enabled by Chiral Carboxylic Acid

Ru­(II)-catalyzed enantioselective C–H functionalization involving an enantiodetermining C–H cleavage step remains undeveloped. Here we describe a Ru­(II)-catalyzed enantioselective C–H activation/annulation of sulfoximines with α-carbonyl sulfoxonium ylides using a novel class of chiral binaphthyl...

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Bibliographic Details
Published in:Journal of the American Chemical Society Vol. 143; no. 18; pp. 6810 - 6816
Main Authors: Zhou, Tao, Qian, Pu-Fan, Li, Jun-Yi, Zhou, Yi-Bo, Li, Hao-Chen, Chen, Hao-Yu, Shi, Bing-Feng
Format: Journal Article
Language:English
Published: United States American Chemical Society 12-05-2021
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Summary:Ru­(II)-catalyzed enantioselective C–H functionalization involving an enantiodetermining C–H cleavage step remains undeveloped. Here we describe a Ru­(II)-catalyzed enantioselective C–H activation/annulation of sulfoximines with α-carbonyl sulfoxonium ylides using a novel class of chiral binaphthyl monocarboxylic acids as chiral ligands, which can be easily and modularly prepared from 1,1′-binaphthyl-2,2′-dicarboxylic acid. A broad range of sulfur-stereogenic sulfoximines were prepared in high yields with excellent enantioselectivities (up to 99% yield and 99% ee) via desymmetrization, kinetic resolution, and parallel kinetic resolution. Furthermore, the resolution products can be easily transformed to chiral sulfoxides and key intermediates for kinase inhibitors.
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ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.1c03111