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Cobalt/Salox-Catalyzed Enantioselective C-H Functionalization of Arylphosphinamides.

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Affiliations

  • 1. Center of Chemistry for Frontier Technologies, Department of Chemistry, Zhejiang University, Hangzhou, 310027, China.
      Authors
    • Yao QJ 1
    • Chen JH 1
    • Song H 1
    • Huang FR 1
    • Shi BF 1
    (5 authors)

ORCIDs linked to this article

Angewandte Chemie (International ed. in English), 21 Apr 2022, 61(25):e202202892
https://doi.org/10.1002/anie.202202892 PMID: 35385597 

Abstract 

Previous methods on CoIII -catalyzed asymmetric C-H activation rely on the use of tailor-made cyclopentadienyl-ligated CoIII complexes, which require lengthy steps for the preparation. Herein, we report an unprecedented enantioselective C-H functionalization enabled by a simple cobalt/salicyloxazoline (Salox) catalysis. The chiral Salox ligands can be easily prepared in one step from salicylonitrile and chiral amino alcohols. A broad range of P-stereogenic compounds were synthesized in high yields with excellent enantioselectivities (45 examples, up to 99 % yield and >99 % ee). The isolation and characterization of several intermediates provided insights into the generation of active catalytic cobalt species, the action of Salox, and the mode of stereocontrol.

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Read article at publisher's site: https://doi.org/10.1002/anie.202202892

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Funding 

Funders who supported this work.

National Natural Science Foundation of China (1)

Natural Science Foundation of Zhejiang Province (1)

Postdoctoral Research Foundation of China (2)