Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 143, Issue 18, Pages 6810-6816Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.1c03111
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Funding
- National Natural Science Foundation of China [21925109, 21772170, 21801223]
- Outstanding Young Talents of Zhejiang Province High-Level Personnel of Special Support [ZJWR0108]
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An undeveloped Ru(II)-catalyzed enantioselective C-H functionalization involving an enantiodetermining C-H cleavage step has been described in this study. Using a novel class of chiral binaphthyl monocarboxylic acids as chiral ligands, a broad range of sulfur-stereogenic sulfoximines were synthesized 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 into chiral sulfoxides and key intermediates for kinase inhibitors.
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 alpha-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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