Lewis Acid-Assisted Formal C═S Insertion of Thioindolinones to Bicyclobutanes: Diastereoselective Access to Trisubstituted Cyclobutanethiols

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-09-16 DOI:10.1021/acs.orglett.5c03564

Palash Roy, , , Shiksha Deswal, , and , Akkattu T. Biju*,

引用次数: 0

Abstract

Although a variety of nucleophilic approaches have been utilized to access substituted cyclobutanes, the synthesis of cyclobutanethiols remains underexplored within the realm of bicyclo[1.1.0]butane (BCB) chemistry. Herein, we report a Lewis acid-assisted C═S insertion of thioindolinones into BCBs, enabling efficient access to a diverse range of 1,3,3-trisubstituted cyclobutanethiols in high diastereoselectivity. The transformation proceeds via a Lewis acid-promoted cascade comprising the (3 + 2) annulation of BCBs with the C═S moiety of thioindolinones followed by the aromaticity-driven ring-opening sequence.

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Lewis酸辅助硫代吲哚酮在双环丁烷上的形式C = S插入：三取代环丁烷硫醇的非对映选择性。

尽管各种亲核方法已被用于获得取代的环丁烷，但在双环[1.1.0]丁烷（BCB）化学领域内，环丁烷硫醇的合成仍未得到充分的探索。在这里，我们报道了路易斯酸辅助C = S将硫代吲哚酮插入到bcb中，使得在高非对对选择性下有效地获得各种1,3,3-三取代环丁烷硫醇。转化通过路易斯酸促进的级联进行，包括（3 + 2）环的bcb与硫代吲哚酮的C = S部分，然后是芳香驱动的开环序列。

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.