Catalytic asymmetric chemoselective 1,3-dipolar cycloadditions of an azomethine ylide with isatin-derived imines: diastereo- and enantioselective construction of a spiro[imidazolidine-2,3′-oxindole] framework

被引：159

作者：

Wang, Yue-Ming ^{[1
]}

Zhang, Hong-Hao ^{[1
]}

Li, Can ^{[1
]}

Fan, Tao ^{[1
]}

Shi, Feng ^{[1
]}

机构：

[1] Jiangsu Normal Univ, Sch Chem & Chem Engn, Xuzhou 221116, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2016年 / 52卷 / 09期

关键词：

BRONSTED ACID; ONE-POT; ORIENTED SYNTHESIS; DERIVATIVES; IMIDAZOLIDINES; NITROALKENES; ALDEHYDES; ESTERS; STRATEGIES; OXINDOLES;

D O I：

10.1039/c5cc07924a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A catalytic asymmetric chemoselective 1,3-dipolar cycloaddition (1,3-DC) of an azomethine ylide with imines has been established via a three-component reaction of isatin-derived imines, aldehydes and an amino-ester in the presence of chiral phosphoric acid, which efficiently constructed biologically important spiro[imidazolidine-2,3'-oxindole] frameworks in good yields, and with high diastereo- and enantioselectivities (up to 76% yield, 97: 3 er, all >95: 5 dr). This reaction not only realized a catalytic asymmetric chemoselective 1,3-DC of an azomethine ylide, but also represented the first enantioselective construction of a spiro[imidazolidine-2,3'-oxindole] skeleton.

引用

页码：1804 / 1807

页数：4

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