A Synthetic Protocol of Trans-Substituted Cyclopentenes via the Ring-Opening Rearrangement of MCP Alkenyl Derivatives

A efficient method to stereospecifically synthesize trans-substituted cyclopentene derivatives via the ring-opening rearrangement of readily available MCP alkenyl derivatives in moderate to good yields has been described. The control experiment based on the deuterium labeling experiment and the addition of TEMPO revealed that this transformation might proceed through a fast concerted pericyclic process rather than a simple radical pathway or an ionic pathway.

本研究报道了一种立体专一性合成反式取代环戊烯衍生物的高效方法，该方法通过对易获取的MCP烯基衍生物进行开环重排反应，可获得中等至优良的反应收率。基于氘标记实验与四甲基哌啶氮氧自由基（TEMPO）添加实验的对照研究表明，该转化过程可能经由快速协同周环反应路径进行，而非简单的自由基路径或离子路径。