Cobalt(III)-Catalyzed Enantioselective Intermolecular Carboamination by C-H Functionalization

Kristers Ozols; Shunsuke Onodera; Łukasz Woźniak; Nicolai Cramer

doi:10.1002/anie.202011140

Cobalt(III)-Catalyzed Enantioselective Intermolecular Carboamination by C-H Functionalization

Angew Chem Int Ed Engl. 2021 Jan 11;60(2):655-659. doi: 10.1002/anie.202011140. Epub 2020 Nov 10.

Authors

Kristers Ozols¹, Shunsuke Onodera^{1

2}, Łukasz Woźniak¹, Nicolai Cramer¹

Affiliations

¹ Institute of Chemical Sciences and Engineering (ISIC), EPFL SB ISIC LCSA, BCH 4305, 1015, Lausanne, Switzerland.
² Department of Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama, 223-8522, Japan.

PMID: 32986927
DOI: 10.1002/anie.202011140

Abstract

High-valent cyclopentadienyl cobalt catalysis is a versatile tool for sustainable C-H bond functionalizations. To harness the full potential of this strategy, control of the stereoselectivity of these processes is necessary. Herein, we report highly enantioselective intermolecular carboaminations of alkenes through C-H activation of N-phenoxyamides catalyzed by Co^III -complexes equipped with chiral cyclopentadienyl (Cp^x ) ligands. The method converts widely available acrylates as well as bicyclic olefins into attractive enantioenriched isotyrosine derivatives as well as elaborated amino-substituted bicyclic scaffolds under very mild conditions. The outlined reactivity is unique to the Cp^x Co^III complexes and is complementary to the reactivity of 4d- and 5d- precious-metal catalysts.

Keywords: C−H functionalization; asymmetric catalysis; carboamination; chiral cyclopentadienyl; cobalt.

Abstract

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