1207340-49-5Relevant articles and documents
Enantioselective Synthesis of 3-Substituted 3-Amino-2-oxindoles by Amination with Anilines
Yang, Wenkun,Dong, Pei,Xu, Jian,Yang, Jian,Liu, Xiaohua,Feng, Xiaoming
supporting information, p. 9272 - 9275 (2021/06/01)
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.
Highly enantioselective synthesis of 3-amino-2-oxindole derivatives: Catalytic asymmetric α-amlnation of 3-substituted 2-oxindoles with a chiral scandium complex
Yang, Zhigang,Wang, Zhen,Bai, Sha,Shen, Ke,Chen, Donghui,Liu, Xiaohua,Lin, Lili,Feng, Xiaoming
supporting information; experimental part, p. 6632 - 6637 (2010/08/20)
A highly enantioselective α-amination of 3-substituted oxindoles with azodicarboxylates catalyzed by a chiral Sc(OTf)3/N,/N′-dioxide complex (Tf: triflate) has been developed and affords the corresponding 3-amino-2-oxindole derivatives in high yields (up to 98%) with excellent enantioselectivities (up to 99% ee). The procedure is capable of tolerating a relatively wide range of substrates, and excellent results (92-96 % ee) can also be obtained, even in the presence of 0.5 mol % of catalyst loading under mild conditions. These results showed the potential value of the catalytic approach. Moreover, with high synthetic versatility, the product could be easily transformed into optically active 3-amino-3-methyloxindole bearing a chiral quaternary stereogenic center.
