Light-Initiated Four-Step Domino-Multicomponent Synthesis of Functionalized Alkylidenecyclobutanes

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2024-11-12 DOI:10.1021/acs.orglett.4c03741

Xiaodan Yu, Arthur Desvals, Zong Chang, Vincent Orève, David J. Aitken, Thomas Boddaert

引用次数: 0

Abstract

A four-step domino-multicomponent reaction (domino-MCR) is described for the synthesis of functionalized E-alkylidenecyclobutanes from 4-hydroxy-2-methylcyclopent-2-enone derivatives and three other simple reagents. The domino-MCR is accomplished in a single protocol, comprising a tandem photochemical [2 + 2]-cycloaddition/Norrish-I/γ-H transfer reaction followed by an acetal protection and an allylic substitution reaction. In parallel, a consecutive process has been established with distinct photochemical and nonradiative sequences. An intramolecular version of these reactions provides access to complex fused-bicyclic alkylidenecyclobutanes.

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光引发的功能化亚烷基环丁烷四步多组分合成法

本文介绍了一种四步多米诺-多组分反应（domino-MCR），用于从 4-羟基-2-甲基环戊-2-烯酮衍生物和其他三种简单试剂合成官能化 E-亚烷基环丁烷。domino-MCR 在单一方案中完成，包括串联光化学 [2 + 2]-cycloaddition/Norrish-I/γ-H 转移反应，然后是乙缩醛保护和烯丙基取代反应。与此同时，还建立了一个具有不同光化学和非辐射序列的连续过程。这些反应的分子内版本提供了获得复杂的融合双环亚烷基环丁烷的途径。

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.