Efficient Synthesis of Chiral Trisubstituted 1,2-Allenyl Ketones by Catalytic Asymmetric Conjugate Addition of Malonic Esters to Enynes

被引：106

作者：

Yao, Qian ^{[1
]}

Liao, Yuting ^{[1
]}

Lin, Lili ^{[1
]}

Lin, Xiaobin ^{[1
]}

Ji, Jie ^{[1
]}

Liu, Xiaohua ^{[1
]}

Feng, Xiaoming ^{[1
,2
]}

机构：

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

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

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2016年 / 55卷 / 05期

基金：

中国国家自然科学基金;

关键词：

1,2-allenyl ketones; 5-hydroxypyrazoline; asymmetric catalysis; enyne addition; furans; ENANTIOSELECTIVE SYNTHESIS; MICHAEL ADDITION; ALLENES; DERIVATIVES; ALLENOATES; AMINATION; LIGANDS; AGENTS; 2,3-ALLENOATES; ALLENYLSILANES;

D O I：

10.1002/anie.201509455

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An N,N'-dioxide/scandium(III) complex catalyzed, highly efficient conjugate addition of malonic esters to enynes is described. A range of trisubstituted 1,2-allenyl ketones were obtained in high yields (up to 99%) with good d.r. (up to 95/5) and excellent ee values (97%-99%). Moreover, the products could be easily transformed into chiral furan and 5-hydroxypyrazoline derivatives, both of which are important skeletons of many biologically active compounds and pharmacologicals.

引用

页码：1859 / 1863

页数：5

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