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  • Title: Nickel-Catalyzed Regio- and Enantioselective Hydroamination of Unactivated Alkenes Using Carbonyl Directing Groups.
    Author: Lee C, Kang HJ, Seo H, Hong S.
    Journal: J Am Chem Soc; 2022 May 25; 144(20):9091-9100. PubMed ID: 35538676.
    Abstract:
    The asymmetric addition of an N-H bond to various alkenes via a direct catalytic method is a powerful way of synthesizing value-added chiral amines. Therefore, the enantio- and regioselective hydroamination of unactivated alkenes remains an appealing goal. Here, we report the highly enantio- and regioselective Ni-catalyzed hydroamination of readily available unactivated alkenes bearing weakly coordinating native amides or esters. This method succeeds for both terminal and internal unactivated alkenes and has a broad amine coupling partner scope. The mild reaction process is well suited for the late-stage functionalization of complex molecules and has the potential to gain modular access to enantioenriched β- or γ-amino acid derivatives and 1,2- or 1,3-diamines. Mechanistic studies reveal that a chiral bisoxazoline-bound Ni specie effectively leverages carbonyl coordination to achieve enantio- and regioselective NiH insertion into alkenes.
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