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Contrasted effect of CO on the metal‐catalyzed cycloisomerization of O‐tethered enynes derived from monoterpenes
Author(s) -
FuenteHernàndez Ariadna,
Costes Philippe,
Kalck Philippe,
JáureguiHaza Ulises,
DechyCabaret Odile,
Urrutigoïty Martine
Publication year - 2011
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.1844
Subject(s) - cycloisomerization , chemistry , enyne , catalysis , alkyne , ligand (biochemistry) , stereochemistry , medicinal chemistry , metal , organic chemistry , receptor , biochemistry
The CO‐bubbling effect in cycloisomerization reactions of enynes derived from monoterpenes has been studied using PtCl 2 , [Rh 2 Cl 2 (CO) 4 ] and AuCl 3 as catalytic systems. All the precursors are efficient catalysts for the cycloisomerization of O‐tethered enynes. The reaction proceeds through exo‐dig and endo‐dig pathways, which are consistent with the exclusive coordination of the alkyne triple bond to the metal center. The CO ligand not only increases the reaction rates but also induces significant variations in the two reaction pathways. Notably, this effect is also strongly dependent on the nature of the starting enyne. Copyright © 2011 John Wiley & Sons, Ltd.