Palladium-catalyzed double strain-release (3+3) cycloaddition for the synthesis of vinylbicyclo[3.1.1]heptanes

IF 4.6 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Chemistry Frontiers Pub Date : 2025-04-24 DOI:10.1039/d5qo00460h

Xin-Yu Gao, Yuanjiu Xiao, Xuan Zhan, Yu-Jie Li, Kun-Ju Wang, Jian-Jun Feng

引用次数: 0

Abstract

All-carbon bicyclo[3.1.1]heptanes are important structural motifs in bioactive compounds and serve as bioisosteres for substituted benzenes. However, their synthesis, especially through polar (3+3) cycloaddition strategies, remains underexplored. Herein, we present a palladium-catalyzed double strain-release (3+3) cycloaddition involving bicyclo[1.1.]butanes (BCBs) and vinylcyclopropanes. The reaction tolerates a variety of BCBs and vinylcyclopropane derivatives, including spirovinylcyclopropane oxindoles, providing access to structurally diverse BCHeps with potential applications in drug discovery. The practicality of this method is demonstrated through scale-up reactions and downstream transformations of the cycloadducts.

查看原文本刊更多论文

钯催化双应变释放 (3+3) 环加成法合成乙烯基双环[3.1.1]庚烷

全碳双环[3.1.1]庚烷是生物活性化合物中的重要结构基序，是取代苯的生物同位体。然而，它们的合成，特别是通过极性（3+3）环加成策略，仍然没有得到充分的探索。在此，我们提出了一种钯催化的双应变释放（3+3）环加成反应，涉及二环[1.1.]丁烷（BCBs）和乙烯基环丙烷。该反应耐受多种BCB和乙烯基环丙烷衍生物，包括螺乙烯基环丙羟吲哚，提供了结构多样的BCHep，在药物发现中具有潜在应用。通过环加合物的放大反应和下游转化，证明了该方法的实用性。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

求助全文

约1分钟内获得全文求助全文

来源期刊

Organic Chemistry Frontiers CHEMISTRY, ORGANIC-

CiteScore

7.90

自引率

11.10%

发文量

686

审稿时长

1 months

期刊介绍： Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.