Asymmetric synthesis of 3-substituted indole derivatives containing tetrahydrothiophene via cascade sulfa-Michael/Michael additions catalyzed by a chiral squaramide catalyst

被引：13
|
作者：
Li, Ying-He [1 ]
Zhao, Bo-Liang [1 ]
Gao, Yu [1 ]
Du, Da-Ming [1 ]
机构：
[1] Beijing Inst Technol, Sch Chem Engn & Environm, Beijing 100081, Peoples R China
来源：
TETRAHEDRON-ASYMMETRY | 2014年 / 25卷 / 23期
基金：
中国国家自然科学基金;
关键词：
ENANTIOSELECTIVE MICHAEL-ADDITION; WATER MARINE SPONGE; BIOLOGICAL EVALUATION; FACILE SYNTHESIS; CONSTRUCTION;
D O I：
10.1016/j.tetasy.2014.10.012
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
The organocatalyzed enantioselective cascade sulfa-Michael/Michael addition reaction of (E)-3-mercapto-2-butenoic acid esters to (E)-3-aryl-2-(indol-3-ylcarbonyl)acrylonitriles has been developed. This process was promoted by a chiral squaramide catalyst to afford chiral 3-substituted indole derivatives containing tetrahydrothiophene with three contiguous stereocenters in excellent diastereoselectivities (up to >20:1 dr) with moderate to good yields and enantioselectivities (up to 93%, 89% ee). (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1513 / 1519
页数：7
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