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
收藏
页码：4077 / 4081
页数：5
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