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

Haijian Wu , Manman Sun , Jing Zhang , Zhiming Wang , Jianguo Yang , Gangguo Zhu
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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 enables the rapid construction of spiro-BCHs in good to excellent yields with a broad substrate scope. Easy scale-up synthesis, potential applications in the modification of bioactive products, mild reaction conditions and simple operation are its 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。
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