4.8 Article

Enantioselective C(sp3)-H Amidation of Thioamides Catalyzed by a CobaltIII/Chiral Carboxylic Acid Hybrid System

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 4, Pages 1153-1157

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201812215

Keywords

asymmetric catalysis; C-H activation; chiral carboxylic acids; cobalt; thioamide

Funding

  1. JSPS KAKENHI [JP15H05802, JP18H04637, JP17H03049, JP17K15417]
  2. Asahi Glass Foundation
  3. Naito Foundation

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Recent advances in (CpMIII)-M-x catalysis (M=Co, Rh, Ir) have enabled a variety of enantioselective C(sp(2))-H functionalization reactions, but enantioselective C(sp(3))-H functionalization is still largely unexplored. We describe an asymmetric C(sp(3))-H amidation of thioamides using an achiral Co-III/chiral carboxylic acid hybrid catalytic system, which provides easy and straightforward access to chiral beta-amino thiocarbonyl and beta-amino carbonyl building blocks with a quaternary carbon stereocenter.

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