HFIP-promoted formal [2π + 2σ] cycloaddition of para-quinone methides with bicyclo[1.1.0]butanes: approach to spiro-bicyclo[2.1.1]hexanes

IF 4.6 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Chemistry Frontiers Pub Date : 2025-01-21 DOI:10.1039/d4qo02226b

Haijian Wu, Manman Sun, Jing Zhang, Zhiming Wang, Jianguo Yang, Gangguo Zhu

引用次数: 0

Abstract

A formal [2π + 2σ] cycloaddition of BCBs with p-QMs has been developed using a small amount of HFIP (2 M) as the solvent without an additional catalyst, in which HFIP also served as a H-bond donor and a cationic stabilizer. This protocol provides a rapid construction of spiro-BCHs in good to excellent yields with a broad substrate scope. Easy scale-up synthesis, potential application in modifications of bioactive products, mild reaction conditions and simple operation show practical advantages.

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hfip促进对醌类化合物与双环[1.1.0]丁烷的形式[2π + 2σ]环加成反应：与螺环-双环[2.1.1]己烷的近似

采用少量HFIP （2 M）作为溶剂，在不添加催化剂的情况下，HFIP同时作为氢键供体和阳离子稳定剂，制备了一种[2π + 2σ]形式的环加成bcb - p-QMs。该方案提供了螺- bchs的快速构建，具有良好的产量和广泛的底物范围。易于规模化合成、在生物活性产品改性方面具有潜在的应用前景、反应条件温和、操作简单等优点。

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 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.