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Bicyclo[2.1.1]hexanes by Visible Light-Driven Intramolecular Crossed [2 + 2] Photocycloadditions
Organic Letters ( IF 4.9 ) Pub Date : 2022-11-22 , DOI: 10.1021/acs.orglett.2c03606
Thomas Rigotti 1 , Thorsten Bach 1
Affiliation  

Bicyclo[2.1.1]hexanes have become increasingly popular building blocks in medicinal chemistry as bridged scaffolds that provide unexplored chemical space. We herein report a visible light-driven approach to these compounds that relies on an intramolecular crossed [2 + 2] photocycloaddition of styrene derivatives enabled by triplet energy transfer. Bicyclo[2.1.1]hexanes were obtained in good to high yields (19 examples, 61%-quantitative yield) and allowed for further functionalizations by consecutive reactions, thereby opening different pathways to decorate the aliphatic core structure.

中文翻译:

双环 [2.1.1] 己烷通过可见光驱动的分子内交叉 [2 + 2] 光环加成

双环 [2.1.1] 己烷已成为药物化学中越来越受欢迎的构件,作为提供未开发化学空间的桥接支架。我们在此报告了一种可见光驱动的方法来处理这些化合物,该方法依赖于通过三线态能量转移实现的苯乙烯衍生物的分子内交叉 [2 + 2] 光环加成。双环 [2.1.1] 己烷的收率从好到高(19 个例子,61% 的定量收率),并允许通过连续反应进一步功能化,从而打开不同的途径来修饰脂肪族核心结构。
更新日期:2022-11-22
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