Institute of Organic Chemistry (IOC), Karlsruhe Institute of Technology (KIT), Fritz-Haber-Weg 6, 76131 Karlsruhe, Germany.
Nat Prod Rep. 2020 Feb 26;37(2):224-245. doi: 10.1039/c8np00086g.
Covering: 1978 to 2019 The synthetically challenging [3.3.3]propellane core has caught a lot of attention over the last 50 years. This comprehensive review details all synthetic strategies reported in the period 1978-2019 to facilitate the synthesis of carbocyclic [3.3.3]propellanes. The described strategies span from acid-catalyzed rearrangements and photo-mediated cycloadditions of ketones, heteropropellanes and dispiroundecanes to thermal rearrangements of acetylenes and alkenes. Other approaches, such as radical reactions with halogenated alkenes, domino cyclizations, the smart use of epoxide-carbonyl rearrangements and intramolecular palladium-catalyzed ring contractions are discussed as well. A special section is dedicated to triptindanes, a subclass of [3.3.3]propellanes which are of interest to material sciences.
1978 年至 2019 年
在过去的 50 年中，具有合成挑战性的[3.3.3]螺旋桨核心引起了很多关注。这篇全面的综述详细介绍了 1978-2019 年期间报道的所有合成策略，以促进碳环[3.3.3]螺旋桨的合成。所描述的策略涵盖了从酮、杂螺旋桨和双环十一烷的酸催化重排和光介导环加成，到炔烃和烯烃的热重排。其他方法，如与卤代烯烃的自由基反应、串联环化、巧妙利用环氧羰基重排和分子内钯催化的环收缩也进行了讨论。还有一个专门的部分介绍了三苯并[3.3.3]螺旋桨，这是一类对材料科学有兴趣的螺旋桨。
