Highly Enantioselective Synthesis of α-Stereogenic Esters through Catalytic Asymmetric Michael Addition of 4-Oxo-4-arylbutenoates

被引：34

作者：

Wang, Zhen ^{[1
]}

Chen, Donghui ^{[1
]}

Yang, Zhigang ^{[1
]}

Bai, Sha ^{[1
]}

Liu, Xiaohua ^{[1
]}

Lin, Lili ^{[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] Sichuan Univ, State Key Lab Oral Dis, Chengdu 610064, Peoples R China

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2010年 / 16卷 / 33期

基金：

中国国家自然科学基金;

关键词：

asymmetric catalysis; chirality; enantioselectivity; Michael addition; scandium; FRIEDEL-CRAFTS ALKYLATION; ELECTRON-POOR ALKENES; BETA-KETO-ESTERS; CONJUGATE ADDITION; ONE-POT; DERIVATIVES; INDOLES; NITROALKANES; ALDIMINES; COMPLEXES;

D O I：

10.1002/chem.201001129

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Highly enantioselective Michael addition of 1,3-dicarbonyl compounds and nitromethane to 4-oxo-4-arylbutenoates catalyzed by N,N'-dioxide-Sc(OTf)(3) complexes has been developed. Using 0.5-2 mol% catalyst loading, various alpha-stereogenic esters were obtained regioselectively with excellent yields (up to 97%) and enantio-selectivities (up to > 99% ee). More-over, the reaction performed well under nearly solvent-free conditions. The products with functional groups are ready for further transformation, which showed the potential value of the catalytic approach. According to the experimental results and previous reports, a plausible working model has been proposed to explain the origin of the activation and the asymmetric induction.

引用

页码：10130 / 10136

页数：7

共 59 条

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