4.8 Article

Versatile Cobalt-Catalyzed Enantioselective Entry to Boryl-Functionalized All-Carbon Quaternary Stereogenic Centers

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 140, Issue 34, Pages 10687-10690

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jacs.8b06814

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Funding

  1. Ministry of Education (MOE) of Singapore [R-143-000-A07-112]

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We report an asymmetric synthesis of chiral boryl-functionalized gamma-lactams containing all-carbon quaternary stereocenters via a Co-catalyzed enantioselective hydroboration/cyclization of amide-tethered 1,6-enynes. These enantio-enriched gamma-lactam products can be readily converted to a variety of cyclic and acyclic other chiral gamma-lactams, pyrrolidin-2,3-diones, beta-amino acid N-carboxyanhydrides, and beta-amino carboxylic amides.

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