Stereocontrolled Construction of the 3,4-Dihydrothiacarbazol-2(9H)-one Skeleton by Using Bifunctional Squaramide-Catalyzed Cascade Reactions

被引：27

作者：

Chen, Shanren ^{[1
]}

Pan, Jianping ^{[1
]}

Wang, Youming ^{[1
]}

Zhou, Zhenghong ^{[1
]}

机构：

[1] Nankai Univ, Collaborat Innovat Ctr Chem Sci & Engn Tianjin, Inst Elementoorgan Chem, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 2014卷 / 35期

基金：

中国国家自然科学基金;

关键词：

Organocatalysis; Domino reactions; Michael addition; Nitrogen heterocycles; Enantioselectivity; Sulfur; FRIEDEL-CRAFTS ALKYLATION; PICTET-SPENGLER REACTIONS; SIMPLE INDOLE ALKALOIDS; DIELS-ALDER REACTION; ENANTIOSELECTIVE SYNTHESIS; EFFICIENT ROUTE; ALPHA; BETA-UNSATURATED ALDEHYDES; MICHAEL ADDITION; TETRAHYDROCARBAZOLES; FUNCTIONALIZATION;

D O I：

10.1002/ejoc.201403078

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient approach for the stereocontrolled construction of the 3,4-dihydrothiacarbazol-2(9H)-one skeleton has been developed. In the presence of a bifunctional squaramide catalyst that was derived from L-tert-leucine, the asymmetric tandem Michael/thiolysis reactions of 9-methylindoline-2-thiones and N-alkynoylphthalimides proceeded efficiently to furnish the desired 3,4-dihydrothiacarbazol-2(9H)-one derivatives in satisfactory yields with high levels of enantioselectivity (up to 98%ee).

引用

页码：7940 / 7947

页数：8

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