Asymmetric Synthesis of Spirocyclic Oxindole-Fused Tetrahydrothiophenes via N,N′-Dioxide-Nickel(II) Catalyzed Domino Reaction of 1,4-Dithiane-2,5-diol with 3-Alkenyloxindoles

被引：46

作者：

Zhou, Pengfei ^{[1
]}

Cai, Yunfei ^{[1
]}

Lin, Lili ^{[1
]}

Lian, Xiangjin ^{[1
]}

Xia, Yong ^{[1
]}

Liu, Xiaohua ^{[1
]}

Feng, Xiaoming ^{[1
,2
]}

机构：

[1] Sichuan Univ, Coll Chem, Minist Educ, Key Lab Green Chem & Technol, Chengdu 610064, Peoples R China

[2] Collaborat Innovat Ctr Chem Sci & Engn, Tianjin, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2015年 / 357卷 / 04期

基金：

中国国家自然科学基金;

关键词：

asymmetric catalysis; N; N '-dioxide-nickel complex; spirooxindoles; tetrahydrothiophenes; HIGHLY ENANTIOSELECTIVE SYNTHESIS; SULFONIUM SULFATE STRUCTURE; STEREOCONTROLLED SYNTHESIS; MULTICOMPONENT CASCADE; FACILE SYNTHESIS; 3+2 ANNULATION; CONSTRUCTION; POTENT; SPIROOXINDOLES; HYDROGENATION;

D O I：

10.1002/adsc.201400964

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A highly efficient chiral N,N'-dioxidenickel(II) complex system has been developed to catalyze the domino thia-Michael/aldol reaction of 1,4-dithiane-2,5-diol with 3-alkenyloxindoles. A series of the desired spirocyclic oxindole-fused tet-rahydrothiophenes was obtained in good yields with excellent ee and dr (up to 97% yield, 98% ee, >19: 1 dr). Besides, based on the X-ray crystal structure of the catalyst as well as the absolute configuration of the product, a catalytic model was proposed to explain the stereocontrol process.

引用

页码：695 / 700

页数：6

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