Asymmetric Michael Addition of Oxindoles to Allenoate Catalyzed by N-Acyl Aminophosphine: Construction of Functionalized Oxindoles with Quaternary Stereogenic Center

被引：46

作者：

Chen, Jinhao ^{[1
,2
]}

Cai, Yuepeng ^{[1
,2
]}

Zhao, Gang ^{[3
]}

机构：

[1] S China Normal Univ, Key Lab Energy Convers & Energy Storage Mat Guang, Sch Chem & Environm, Guangzhou 510006, Guangdong, Peoples R China

[2] S China Normal Univ, Guangzhou 510006, Guangdong, Peoples R China

[3] 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：

allenoates; asymmetric catalysis; chiral phosphines; Michael addition; oxindoles; ENANTIOSELECTIVE 3+2 ANNULATIONS; GAMMA-ADDITION; PHOSPHINE; 2,3-BUTADIENOATES; CYCLOADDITION; NUCLEOPHILES; OLEFINS; CYCLOPENTENES; 2-BUTYNOATES; UMPOLUNG;

D O I：

10.1002/adsc.201300695

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A novel reaction between ethyl allenoate and oxindoles that enables the asymmetric synthesis of 3,3-bisubstituted oxindoles with our previously established bifunctional N-acyl aminophosphine catalysts is reported. These products bearing a chiral quaternary carbon center at the C-3 position of the oxindoles may have potential significance in the synthesis of related structures. The best performance of these processes provides adducts with 92% yield and 94% ee.

引用

页码：359 / 363

页数：5

共 53 条

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[Anonymous], 2013, ANGEW CHEM

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