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  • Title: Nickel-Catalyzed Enantioselective C(sp3)-C(sp3) Cross-Electrophile Coupling of N-Sulfonyl Styrenyl Aziridines with Alkyl Bromides.
    Author: Lan Y, Han Q, Liao P, Chen R, Fan F, Zhao X, Liu W.
    Journal: J Am Chem Soc; 2024 Sep 18; 146(37):25426-25432. PubMed ID: 39231321.
    Abstract:
    Herein, we report the first example of a highly enantioselective alkylative aziridine ring opening. Under the catalysis of a chiral nickel/pyridine-imidazoline complex, asymmetric C(sp3)-C(sp3) cross-electrophile coupling between racemic N-sulfonyl styrenyl aziridines and readily available primary alkyl bromides furnishes a variety of highly enantioenriched phenethylamine derivatives with complete regiocontrol and good functional group tolerance. Preliminary mechanistic studies support a reaction pathway consisting of regioselective iodolysis of aziridines in situ and subsequent enantioconvergent coupling of the generated β-amino benzyl iodides with alkyl bromides.
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