FeCl3-Catalyzed Intermolecular Formal [8π+2σ] Cycloaddition of Azaheptafulvene with Bicyclo[1.1.0]butanes for the Synthesis of Cycloheptatriene-Fused 2-Azabicyclo[3.1.1]heptanes

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-04-08 DOI:10.1021/acs.orglett.5c00489

Shijie Zhu, Jiaojiao Lei, Shengwen Yang, Zhifei Zhao, Ning Liu, Shi-Wu Li

引用次数: 0

Abstract

Higher-order cycloadditions are a simple and effective strategy for constructing significant medium-sized architectures. Azaheptafulvenes reacting with readily accessible bicyclo[1.1.0]butanes (BCBs) through FeCl₃-promoted intermolecular formal [8π+2σ] cycloaddition reactions to access cycloheptatriene-fused 2-azabicyclo[3.1.1]heptanes have been developed. This new reaction tolerated a wide range of azaheptafulvenes and BCBs. Furthermore, the amplification experiment and synthetic transformations of the adducts, including modifications of marketed drugs, further highlighted their practicalities. Control experiments and DFT calculations suggest that the diastereoselective [8π+2σ] product formation may involve a stepwise pathway.

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fecl3催化氮杂七烯与双环[1.1.0]丁烷的分子间形式[8π+2σ]环加成合成环庚三烯- 2-氮杂环[3.1.1]庚烷

对于构建重要的中等规模的体系结构，高阶循环加法是一种简单而有效的策略。通过fecl3促进的分子间形式[8π+2σ]环加成反应，制备了偶氮七环[3.1.1]庚烷与易接近的双环[1.1.0]丁烷（BCBs）反应。这种新反应耐受广泛的氮杂七烯和bcb。此外，这些加合物的扩增实验和合成转化，包括对已上市药物的修饰，进一步突出了它们的实用性。控制实验和DFT计算表明，非对向选择性[8π+2σ]产物的形成可能涉及一个逐步的途径。

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.