Synthesis of Spiro[chroman/tetrahydrothiophene-3,3′-oxindole] Scaffolds via Heteroatom-Michael-Michael Reactions: Easily Controlled Enantioselectivity via Bifunctional Catalysts

被引：52
|
作者：
Huang, Youming [1 ]
Zheng, Changwu [1 ]
Chai, Zhuo [1 ]
Zhao, Gang [1 ]
机构：
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Synthet Chem Nat Subst, Shanghai 200032, Peoples R China
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2014年 / 356卷 / 2-3期
基金：
中国国家自然科学基金;
关键词：
asymmetric catalysis; cascade reactions; heteroatom-Michael-Michael reaction; organocatalysis; spirooxindoles; NATURAL-PRODUCTS; CONSTRUCTION; STEREOCENTERS; EFFICIENT; ISATINS;
D O I：
10.1002/adsc.201300833
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
An efficient method for the construction of chiral spirooxindole-chroman and spirooxindole-tetrahydrothiophene scaffolds with three consecutive chiral centers including an all-carbon quaternary spirocenter has been developed. This method features an asymmetric thia/oxa-Michael-Michael cascade sequence in a single operation in the presence of chiral tertiary amine-thioureas as the catalysts, providing the desired products in good chemical yields and optical purities.
引用
收藏
页码：579 / 583
页数：5
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