A Synthetic Route to Chiral Tetrahydropyrroloindoles via Ring Opening of Activated Aziridines with 2-Bromoindoles Followed by Copper-Catalyzed C-N Cyclization

被引：28

作者：

Sayyad, Masthanvali ^{[1
]}

Mal, Abhijit ^{[1
]}

Wani, Imtiyaz Ahmad ^{[1
]}

Ghorai, Manas K. ^{[1
]}

机构：

[1] Indian Inst Technol, Dept Chem, Kanpur 208016, Uttar Pradesh, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 81卷 / 15期

关键词：

LEWIS-ACID; ASYMMETRIC CONSTRUCTION; TRYPTAMINE DERIVATIVES; BOND FORMATION; PYRROLOINDOLINES; INDOLES; TRYPTOPHAN; REACTIVITY; 2,3-DIHYDROPYRROLO<2,3-B>INDOLES; SULFONYLAZIRIDINES;

D O I：

10.1021/acs.joc.6b01049

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new synthetic route to nonracemic tetrahydropyrrolo[2,3-b]indoles has been developed via S(N)2-type ring opening of enantiopure N-activated aziridines with 2-bromoindoles followed by copper-catalyzed C-N cyclization. A series of N-activated aziridines and 2-bromoindole derivatives with different substitution patterns were studied to afford the corresponding tetrahydropyrrolo[2,3-b]indoles in good yields and excellent ee (up to 99%). Highly substituted tetrahydropyrrolo[2,3-b]indole was synthesized as a single stereoisomer (de, ee >99%) from enantiopure trans-disubstituted aziridine.

引用

页码：6424 / 6432

页数：9

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