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. 2020 Feb 3;59(6):2328-2332.
doi: 10.1002/anie.201913743. Epub 2019 Dec 27.

Nickel-Catalyzed Asymmetric Reductive 1,2-Carboamination of Unactivated Alkenes

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Nickel-Catalyzed Asymmetric Reductive 1,2-Carboamination of Unactivated Alkenes

Jun He et al. Angew Chem Int Ed Engl. .

Abstract

Starting from diverse alkene-tethered aryl iodides and O-benzoyl-hydroxylamines, the enantioselective reductive cross-electrophilic 1,2-carboamination of unactivated alkenes was achieved using a chiral pyrox/nickel complex as the catalyst. This mild, modular, and practical protocol provides rapid access to a variety of β-chiral amines with an enantioenriched aryl-substituted quaternary carbon center in good yields and with excellent enantioselectivities. This process reveals a complementary regioselectivity when compared to Pd and Cu catalysis.

Keywords: alkenes; asymmetric catalysis; carboamination; nickel; synthetic methods.

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References

    1. For selected reviews, see:
    1. W. S. Knowles, Angew. Chem. Int. Ed. 2002, 41, 1998;
    1. Angew. Chem. 2002, 114, 2096;
    1. R. Noyori, Angew. Chem. Int. Ed. 2002, 41, 2008;
    1. Angew. Chem. 2002, 114, 2108.

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