Stereoselective Alkyne–Alkene [2 + 2] Cycloaddition Enabled by Anion Relay Chemistry for Fully C-Substituted Cyclobutene Synthesis

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-02-06 DOI:10.1021/acs.orglett.4c0425510.1021/acs.orglett.4c04255

Xiaomeng Gong, Rui-Peng Li, Xiangrong Xu, Guohong Tang and Shouchu Tang*,

引用次数: 0

Abstract

Cyclobutenes serve as valuable scaffolds in pharmaceutical development, but synthesizing structurally diverse fully C-substituted cyclobutenes remains challenging. Here we report a stereoselective [2 + 2] cycloaddition between alkynyl 1,3-dithianes and cinnamate esters using a catalytic amount of KOtBu. Our approach enables the construction of synthetically challenging tetrasubstituted cyclobutenes via anion relay chemistry (ARC), exhibiting excellent trans-diastereoselectivities (dr > 20:1).

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阴离子接力化学使立体选择性炔-烯烃[2 + 2]环加成合成全c取代环丁烯

环丁烯在药物开发中是有价值的支架，但合成结构多样的全c取代环丁烯仍然具有挑战性。在这里，我们报道了用催化量的KOtBu在炔基1,3-二硫烷和肉桂酸酯之间进行立体选择性[2 + 2]环加成反应。我们的方法能够通过阴离子接力化学（ARC）构建具有合成挑战性的四取代环丁烯，表现出优异的反-非对映选择性(dr >；20:1)。

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.