Dearomative (3+2) Cycloaddition of Indoles for the Stereoselective Assembly of Fully Functionalized Cyclopentanoids

被引：0

作者：

Al-Khdhairawi, Amjad Ayad Qatran ^{[1
]}

Yuan, Tengrui ^{[1
,2
]}

Van Hecke, Kristof ^{[3
]}

Winne, Johan M. ^{[1
]}

机构：

[1] Univ Ghent, Dept Organ & Macromol Chem, B-9000 Ghent, Belgium

[2] Yunnan Precious Met Lab Co Ltd, Kunming 650106, Yunnan, Peoples R China

[3] Univ Ghent, Dept Chem, XStruct, B-9000 Ghent, Belgium

来源：

ORGANIC LETTERS | 2024年 / 26卷 / 19期

基金：

中国国家自然科学基金;

关键词：

ANNULATION;

D O I：

10.1021/acs.orglett.4c01139

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The gold(I)-catalyzed dearomative cyclopentannulation of various indoles with 2-ethynyl-1,3-dithiolane is reported. The method generates three new stereocenters with excellent control of relative stereochemistry and is tolerant of diverse functionalization and substitution patterns on the indoles. The obtained cyclopentane-fused indolines allow for interesting subsequent synthetic manipulations, giving rise to fully substituted cyclopentanes with control of the relative stereochemistry of all five stereocenters. The reported reaction illustrates and elucidates a mechanistic dichotomy underlying gold(I)-catalyzed reactions of 2-ethynyl-1,3-dithiolane.

引用

页码：4077 / 4081

页数：5

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