Eichenberger Sarah, Hönig Moritz, Richter Matthieu J R, Gershoni-Poranne Renana, Carreira Erick M
Laboratorium für Organische Chemie, Eidgenössische Technische Hochschule Zürich, HCI H335 Vladimir-Prelog-Weg 3 8093 Zürich Switzerland
Chem Sci. 2020 May 4;11(20):5294-5298. doi: 10.1039/d0sc02224a.
A novel Lewis acid-catalyzed cycloisomerization of alkylidenecyclopropane acylsilanes is disclosed. The readily available starting materials participate in tandem Prins addition/ring expansion/1,2-silyl shift to grant access to bicyclo[4.2.0]octanes and bicyclo[3.2.0]heptanes, which are common motifs in terpenoid natural products. Notably, the transformation relies on the ability of acylsilanes to act sequentially as acceptors and donors on the same carbon atom.
公开了一种新型的路易斯酸催化的亚烷基环丙烷酰基硅烷的环异构化反应。易于获得的起始原料参与串联的普林斯加成/扩环/1,2-硅基迁移反应，从而得到双环[4.2.0]辛烷和双环[3.2.0]庚烷，它们是萜类天然产物中的常见结构单元。值得注意的是，该转化依赖于酰基硅烷在同一碳原子上依次作为受体和供体的能力。
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