Asymmetric Synthesis of 1,1,1-Triarylethanes by Chiral Imidodiphosphoric Acid Catalyzed Nucleophilic Addition of Pyrrole and Indoles to 3-Vinylindoles

被引:27
作者
Guan, Xu-Kai [1 ]
Zhang, Heng [1 ]
Gao, Ji-Gang [1 ]
Sun, Dong-Yang [1 ]
Qin, Xiang-Shuo [1 ]
Jiang, Guo-Feng [1 ]
Zhang, Guang-Liang [1 ]
Zhang, Suoqin [1 ]
机构
[1] Jilin Univ, Coll Chem, 2699 Qanjin St, Changchun 130012, Jilin, Peoples R China
基金
中国国家自然科学基金; 中国博士后科学基金;
关键词
FRIEDEL-CRAFTS ALKYLATION; DIELS-ALDER REACTION; ENANTIOSELECTIVE SYNTHESIS; ARYLATION;
D O I
10.1021/acs.joc.9b02024
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Chiral imidodiphosphoric acids were employed as efficient catalysts in the enantioselective addition reaction of pyrrole and indoles to 3-vinylindoles. A series of optically active 1,1,1-triarylethmanes bearing quaternary stereocenters were synthesized in excellent yields (up to 99% yield) and enantioselectivities (up to 98% ee). Gram-scale reactions of li and 2a as well as lo and Sa demonstrated the synthetic utility of this methodology. Control experiments showed that the formation of a double H-bond between the catalyst and substrates is necessary for an excellent outcome.
引用
收藏
页码:12562 / 12572
页数:11
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