Synthesis of Cyclopenta[b]indoles via Rhodium-Catalyzed Cascade Migration-Annulation of 1-Sulfonyl-1,2,3-triazoles and Indoles

被引：8

作者：

Xu, Huaping ^{[1
,2
]}

Wang, Heng ^{[1
]}

Xu, Ze-Feng ^{[1
]}

Duan, Shengguo ^{[1
]}

Li, Chuan-Ying ^{[1
]}

机构：

[1] Zhejiang Sci Tech Univ, Sch Chem & Chem Engn, Key Lab Surface & Interface Sci Polymer Mat Zhejia, Hangzhou 310018, Peoples R China

[2] Zhejiang Sci Tech Univ, Sch Mat Sci & Engn, Xiasha West Higher Educ Dist, Hangzhou 310018, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2023年 / 365卷 / 10期

基金：

中国国家自然科学基金;

关键词：

migration-annulation; 1-sulfonyl-1,2,3triazoles; carbenes; cyclopenta[b]indoles; DEAROMATIVE 3+2 CYCLOADDITION; 1,3-DIPOLAR CYCLOADDITIONS; 3-NITROINDOLES; FUNCTIONALIZATION; TRANSANNULATION; 1,2,3-TRIAZOLES; HETEROCYCLES; INDOLINES; CONSTRUCTION; ZWITTERION;

D O I：

10.1002/adsc.202300241

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A rhodium-catalyzed cascade 1,3-sulfinate migration, intermolecular [3 +2] annulation of 1-sulfonyl-1,2,3-triazoles and indoles was achieved. The one-pot protocol provided a method to construct cyclopenta[b]indoles bearing four stereocenters in 45% to 99% yields with 1.6:1 to > 20:1 diastereoselectivities. In addition, cyclopenta[b]indoles could be transformed into a variety of functionalized compounds, demonstrating the synthetic value of this migration-annulation strategy in ring system synthesis.

引用

页码：1623 / 1628

页数：6

共 86 条

[1] Gold-catalyzed heterocyclic syntheses through α-imino gold carbene complexes as intermediates Dedicated to Professor Dr Julius Rebek, Jr. on the occasion of his 75th birthday. [J].