Rüedi Georg, Nagel Matthias, Hansen Hans-Jürgen
Organisch-chemisches Institut der Universität, 8057 Zürich, Switzerland.
Org Lett. 2004 Aug 19;6(17):2989-91. doi: 10.1021/ol0487027.
A thermal three-carbon ring expansion based on side chain ring insertion of a cyclopropane moiety is described. Flash vacuum pyrolysis (FVP) of 1-cyclopropyl-cycloalk-3-enol derivatives leads to the three-carbon ring expanded enones with clean retention of double bond geometry. Substrates bearing methyl groups on the cyclopropane ring undergo regioselective bond cleavage, allowing for the systematic preparation of selectively substituted macrocyclic musks from low-priced C-12 starting compounds.
描述了一种基于环丙烷部分侧链环插入的热三碳环扩展反应。1-环丙基-环烷-3-烯醇衍生物的闪式真空热解（FVP）可生成三碳环扩展的烯酮，双键几何构型完全保持。在环丙烷环上带有甲基的底物会发生区域选择性键断裂，从而能够从低价的C-12起始化合物系统地制备选择性取代的大环麝香。
