Highly Stereoselective Conjugate Addition and -Alkynylation Reaction with Electron-Deficient Alkynes Catalyzed by Chiral Scandium(III) Complexes

被引：31

作者：

Wang, Zhen ^{[1
]}

Zhang, Zuliang ^{[1
]}

Yao, Qian ^{[1
]}

Liu, Xiaohua ^{[1
]}

Cai, Yunfei ^{[1
]}

Lin, Lili ^{[1
]}

Feng, Xiaoming ^{[1
]}

机构：

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

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2013年 / 19卷 / 26期

基金：

中国国家自然科学基金;

关键词：

acetylenic substitution; alkynes; N; N-dioxides; oxindoles; scandium; Z selective; ASYMMETRIC MICHAEL ADDITION; ALPHA-CYANOACETATES; OXINDOLES; ORGANOCATALYSTS; CONSTRUCTION; EFFICIENT; LIGANDS; KETONES; CARBON; BONDS;

D O I：

10.1002/chem.201300816

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The highly Z-selective asymmetric conjugate addition of 3-substituted oxindoles to alkynyl carbonyl compounds has been developed by using scandium complexes of chiral N,N-dioxides under mild conditions. The thermodynamically unstable Z-olefin derivatives were obtained in excellent yields and high enantiomeric and geometric control. The catalyst was also found to be effective in the asymmetric acetylenic substitution reaction of 3-substituted oxindoles, giving excellent enantioselectivities.

引用

页码：8591 / 8596

页数：6

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