Nickel-Catalyzed Enantioselective C(sp<sup>3</sup>)–C(sp<sup>3</sup>) Cross-Electrophile Coupling of <i>N</i>-Sulfonyl Styrenyl Aziridines with Alkyl Bromides
Yun Lan, Qiaoying Han, Pingyong Liao, Ruijia Chen, Fan Fei, Xuejun Zhao, Wenbin Liu
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(sp 3 )–C(sp 3 ) 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.