DMAP 催化乙烯基环氧乙烷与活化酮化合物的开环/环加成反应以构建 1,3-二氧戊环骨架

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2024-10-24 DOI:10.1021/acs.orglett.4c0350210.1021/acs.orglett.4c03502

Jiaxin Qu, Tongtong Yang, Xin Zhao, Chentong Sun, Chunhao Yuan*, Hongchao Guo* and Chang Wang*,

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引用次数: 0

摘要

本研究开发了一种 DMAP 催化的乙烯基环氧乙烷与活化酮化合物的[3 + 2]环加成反应，以中等到极好的收率获得二氧戊环衍生物。该方法代表了首个路易斯碱（LB）催化的乙烯基环氧化物开环反应，同时提供了该领域罕见的含氧活性中间体。环加合物的克级制备和简易衍生化凸显了这一策略的巨大合成潜力。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

DMAP Catalyzed Ring-Opening/Cycloaddition of Vinyl Oxiranes with Activated Ketone Compounds to Construct the 1,3-Dioxolane Skeletons

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DMAP Catalyzed Ring-Opening/Cycloaddition of Vinyl Oxiranes with Activated Ketone Compounds to Construct the 1,3-Dioxolane Skeletons

The present work develops a DMAP-catalyzed [3 + 2] cycloaddition of vinyl oxiranes with activated ketone compounds, affording dioxolane derivatives with moderate to excellent yields. This approach represents the first Lewis base (LB)-catalyzed ring-opening reaction of vinyl epoxides, simultaneously providing a rare oxygen-containing active intermediate in this field. The gram-scale preparation and facile derivatization of the cycloadduct highlight the significant synthetic potential of this strategy.

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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.