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Alkoxyallene‐ynes: Selective Preparation of Bicyclo[5.3.0] Ring Systems Including a δ‐Alkoxy Cyclopentadienone
Author(s) -
Tap Aurélien,
Lecourt Camille,
Dhambri Sabrina,
Arnould Mathieu,
Galvani Gilles,
Nguyen Van Buu Olivier,
Jouanneau Morgan,
Férézou JeanPierre,
Ardisson Janick,
Lannou MarieIsabelle,
Sorin Geoffroy
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201504753
Subject(s) - alkoxy group , moiety , chemistry , diene , bicyclic molecule , intramolecular force , ring (chemistry) , medicinal chemistry , rhodium , ether , enol ether , propane , stereochemistry , catalysis , organic chemistry , alkyl , natural rubber
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 heterobicyclo[5.3.0] 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.