Organocatalytic asymmetric domino Michael/O-alkylation reaction for the construction of succinimide substituted 3(2H)-furanones catalyzed by quinine

被引：11

作者：

Zhou, Jing ^{[1
]}

Bai, Lijuan ^{[1
]}

Liang, Guojuan ^{[1
]}

Chen, Yongjie ^{[1
]}

Gan, Zongjie ^{[1
]}

Wang, Wu ^{[1
]}

Zhou, Hui ^{[1
]}

Yu, Yu ^{[1
]}

机构：

[1] Chongqing Med Univ, Sch Pharmaceut Sci, Chongqing Res Ctr Pharmaceut Engn, Chongqing Key Lab Biochem & Mol Pharmacol, Chongqing 400016, Peoples R China

来源：

RSC ADVANCES | 2017年 / 7卷 / 63期

基金：

中国国家自然科学基金;

关键词：

TETRONIC ACID-DERIVATIVES; INTRAMOLECULAR CYCLIZATION; ENANTIOSELECTIVE SYNTHESIS; EFFICIENT CONSTRUCTION; MANNICH REACTION; MALEIMIDES; CARBON; ACCESS; QUATERNARY; ALDEHYDES;

D O I：

10.1039/c7ra07317h

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A new organocatalytic asymmetric domino Michael/O-alkylation reaction of maleimides with gamma-halogenated-beta-ketoesters catalyzed by simple, cheap, and commercially available quinine is described. The substrates are also commercially available. A variety of new chiral succinimide substituted 3(2H)-furanones were obtained in high yields (up to 94%) and good enantioselectivities (up to 94% ee). The absolute configuration of the new compound 4f was determined by single-crystal X-ray analysis and the proposed reaction pathway is also shown.

引用

收藏

页码：39885 / 39888

页数：4

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