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From Cyclopropene to Housane Derivatives Via Intramolecular Cyclopropanation
Darío Coto1,2,3, David Suárez-García1,2,3, Sergio Mata1
1Departamento de Química Orgánica e Inorgánica, Universidad de Oviedo, Julián Clavería 8, 33006, Oviedo, Spain.
Abstract:
The synthesis of housane derivatives from cyclopropenes is described. Under rhodium(II) catalysis, cyclopropenylvinyl carbinols can regioselectively generate a carbene intermediate which undergoes an intramolecular cyclopropanation to form a housane, a skeleton with similar ring strain as the cyclopropene precursor. The procedure shows a remarkable broad scope and efficiency. Moreover, the method served to prepare man-made housane-containing terpene derivatives, which are not accessible by Nature.
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