Alkoxyallene‐ynes: Selective Preparation of Bicyclo[5.3.0] Ring Systems Including a δ‐Alkoxy Cyclopentadienone |
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| Authors: | Dr Aurélien Tap Camille Lecourt Sabrina Dhambri Mathieu Arnould Dr Gilles Galvani Dr Olivier Nguyen Van Buu Dr Morgan Jouanneau Dr Jean‐Pierre Férézou Prof Janick Ardisson Dr Marie‐Isabelle Lannou Dr Geoffroy Sorin |
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| Affiliation: | 1. Faculté des Sciences Pharmaceutiques et Biologiques, Unité CNRS UMR 8638 COMèTE, Paris Descartes University, Sorbonne Paris Cité, Paris cedex 06, France;2. Laboratoire de Chimie des Procédés et Substances Naturelles, ICMMO (CNRS UMR 8182), Université Paris-Sud, Batiment 410, Orsay Cedex, France |
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| Abstract: | The development of an intramolecular rhodium(I)‐catalyzed Pauson–Khand reaction of alkoxyallene‐ynes with a proximal alkoxy group is reported. This reaction, in the presence of a Rh(cycloocta‐1,5‐diene)Cl]2/propane‐1,3‐diylbis(diphenylphosphane) system under a CO atmosphere, constitutes a powerful tool for selectively accessing carbo‐ and heterobicyclo5.3.0] frameworks featuring an enol ether moiety. Through this procedure, a straightforward access to guaiane skeletons with a tertiary hydroxy group at the C10 position was achieved. |
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| Keywords: | allenes alkynes cyclization Pauson– Khand reactions rhodium |
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