Stereocontrolled construction of the dihydrothiopyrano[2,3-b]indole skeleton via an organocatalyzed asymmetric cascade sulfa-Michael-aldol reaction

被引：12
|
作者：
Wu, Lulu [1 ]
Wang, Youming [1 ]
Zhou, Zhenghong [1 ]
机构：
[1] Nankai Univ, Collaborat Innovat Ctr Chem Sci & Engn Tianjin, Inst & State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China
来源：
TETRAHEDRON-ASYMMETRY | 2014年 / 25卷 / 20-21期
基金：
中国国家自然科学基金;
关键词：
FRIEDEL-CRAFTS ALKYLATION; THIOPYRANO INDOLE-DERIVATIVES; ENANTIOSELECTIVE SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; SIMPLE OXINDOLE; ACCESS; TETRAHYDROTHIOPHENES;
D O I：
10.1016/j.tetasy.2014.09.005
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
We have developed an organocatalyzed asymmetric cascade sulfa-Michael-aldol reaction between 2-mercaptoindole-3-carbaldehydes and enals, which provides efficient access to the stereocontrolled construction of dihydrothiopyrano[2,3-b]indole skeletons. Under the catalysis of chiral diphenylprolinol TMS ether, the reactions ran smoothly to give the corresponding synthetically useful and pharmaceutically valuable dihydrothiopyrano[2,3-b]indoles in high yields and with 64-96% ee. (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1389 / 1395
页数：7
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