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

Angew Chem Int Ed Engl. 2019 Jan 21;58(4):1153-1157. doi: 10.1002/anie.201812215. Epub 2018 Dec 20.

Abstract

Recent advances in Cpx MIII catalysis (M=Co, Rh, Ir) have enabled a variety of enantioselective C(sp2 )-H functionalization reactions, but enantioselective C(sp3 )-H functionalization is still largely unexplored. We describe an asymmetric C(sp3 )-H amidation of thioamides using an achiral CoIII /chiral carboxylic acid hybrid catalytic system, which provides easy and straightforward access to chiral β-amino thiocarbonyl and β-amino carbonyl building blocks with a quaternary carbon stereocenter.

Keywords: C−H activation; asymmetric catalysis; chiral carboxylic acids; cobalt; thioamide.

Publication types

  • Research Support, Non-U.S. Gov't