Enantioselective Synthesis of 3‐Substituted 3‐Amino‐2‐oxindoles by Amination with Anilines

作者：Yang Wen-kun, Pei Dong, Jian Xu, Jian Yang, Xiaohua Liu, Xiaoming Feng · 发表于：Chemistry - A European Journal · 年份：2021 · DOI：10.1002/chem.202100829 · 被引用次数：26 · 研究领域：Asymmetric Synthesis and Catalysis、Synthesis and Catalytic Reactions、Asymmetric Hydrogenation and Catalysis

A chiral N,N'-dioxide-nickel(II) complex-catalyzed asymmetric amination of 3-bromo-3-substituted oxindoles with anilines has been developed. A series of alkyl or aryl 3-amino-indolinones with quaternary stereocenters were obtained in high yields with excellent ee values in one step (up to 99 % yield, up to 96 % ee). The method provided a ready route to optically active intermediates of 3-amino-2-oxindole-based bioactive compounds. Moreover, a possible transition-state model is proposed so as to elucidate the origin of the chirality based on the X-ray crystal structure of the catalyst and the adduct.