Alkoxyallene‐ynes: Selective Preparation of Bicyclo[5.3.0] Ring Systems Including a δ‐Alkoxy Cyclopentadienone | Zendy

Tap Aurélien | Zendy; Lecourt Camille | Zendy; Dhambri Sabrina | Zendy; Arnould Mathieu | Zendy; Galvani Gilles | Zendy; Nguyen Van Buu Olivier | Zendy; Jouanneau Morgan | Zendy; Férézou JeanPierre | Zendy; Ardisson Janick | Zendy; Lannou MarieIsabelle | Zendy; Sorin Geoffroy | Zendy

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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.

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