Gold(I)-Catalyzed Tandem 1,2-Indole Migration–Cyclopropanation Reactions of 3-Propargylindoles with Olefins

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-07-28 DOI:10.1021/acs.orglett.5c02596

Lorena Renedo, Marta Solas, Raquel Hernández-Ruiz, Samuel Suárez-Pantiga and Roberto Sanz*,

引用次数: 0

Abstract

3-Propargylindoles with a terminal alkyne, efficiently prepared from direct alkylation of indoles, undergo a tandem 1,2-indole migration/cyclopropanation reaction under gold(I) catalysis. Reaction conditions have been developed for suitable access to indole-substituted vinylcyclopropanes from 3-propargyl indoles and olefins. The corresponding 2-alkenyl-functionalized substrates evolve through an intramolecular cyclopropanation allowing the synthesis of various polycyclic indole derivatives. The presence of silver salts modifies the diastereoselectivity observed.

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金(I)催化的串联1,2-吲哚迁移- 3-丙炔啉与烯烃的环丙烷化反应。

以吲哚为直接烷基化反应，在金(I)的催化下进行了1,2-吲哚的串联迁移/环丙烷化反应，制备了末端炔的3-丙炔炔醇。建立了由3-丙基吲哚和烯烃制备吲哚取代乙烯基环丙烷的适宜反应条件。相应的2-烯基功能化底物通过分子内环丙烷化进化，从而合成各种多环吲哚衍生物。银盐的存在改变了所观察到的非对映选择性。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.