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Cobalt(III)-Catalyzed Enantioselective Intermolecular Carboamination by C-H Functionalization.
Angew Chem Int Ed Engl. 2021 Jan 11; 60(2):655-659.AC

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 CoIII -complexes equipped with chiral cyclopentadienyl (Cpx) 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 Cpx CoIII complexes and is complementary to the reactivity of 4d- and 5d- precious-metal catalysts.

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Publisher Full Text (DOI)

Authors+Show Affiliations

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

Pub Type(s)

Journal Article

Language

eng

PubMed ID

32986927

Citation

Ozols, Kristers, et al. "Cobalt(III)-Catalyzed Enantioselective Intermolecular Carboamination By C-H Functionalization." Angewandte Chemie (International Ed. in English), vol. 60, no. 2, 2021, pp. 655-659.
Ozols K, Onodera S, Woźniak Ł, et al. Cobalt(III)-Catalyzed Enantioselective Intermolecular Carboamination by C-H Functionalization. Angew Chem Int Ed Engl. 2021;60(2):655-659.
Ozols, K., Onodera, S., Woźniak, Ł., & Cramer, N. (2021). Cobalt(III)-Catalyzed Enantioselective Intermolecular Carboamination by C-H Functionalization. Angewandte Chemie (International Ed. in English), 60(2), 655-659. https://doi.org/10.1002/anie.202011140
Ozols K, et al. Cobalt(III)-Catalyzed Enantioselective Intermolecular Carboamination By C-H Functionalization. Angew Chem Int Ed Engl. 2021 Jan 11;60(2):655-659. PubMed PMID: 32986927.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Cobalt(III)-Catalyzed Enantioselective Intermolecular Carboamination by C-H Functionalization. AU - Ozols,Kristers, AU - Onodera,Shunsuke, AU - Woźniak,Łukasz, AU - Cramer,Nicolai, Y1 - 2020/11/10/ PY - 2020/08/14/received PY - 2020/9/29/pubmed PY - 2020/9/29/medline PY - 2020/9/28/entrez KW - C−H functionalization KW - asymmetric catalysis KW - carboamination KW - chiral cyclopentadienyl KW - cobalt SP - 655 EP - 659 JF - Angewandte Chemie (International ed. in English) JO - Angew Chem Int Ed Engl VL - 60 IS - 2 N2 - 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 CoIII -complexes equipped with chiral cyclopentadienyl (Cpx) 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 Cpx CoIII complexes and is complementary to the reactivity of 4d- and 5d- precious-metal catalysts. SN - 1521-3773 UR - https://www.unboundmedicine.com/medline/citation/32986927/Cobalt_III__Catalyzed_Enantioselective_Intermolecular_Carboamination_by_C_H_Functionalization_ DB - PRIME DP - Unbound Medicine ER -