Ene-yne-ene and ene-yne-yne metathesis of norbornene derivatives

Norbornene derivatives 4 and 5 containing sidechains bearing an internal alkyne and either a terminal alkene or a terminal alkyne were found to undergo a cascade of metathesis reactions when treated with ruthenium based metathesis catalysts to form highly functionalised pentacyclic products. The rea...

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Bibliographic Details
Published in:Tetrahedron letters 2003-10, Vol.44 (44), p.8157-8160
Main Authors: Banti, Donatella, North, Michael
Format: Article
Language:English
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Summary:Norbornene derivatives 4 and 5 containing sidechains bearing an internal alkyne and either a terminal alkene or a terminal alkyne were found to undergo a cascade of metathesis reactions when treated with ruthenium based metathesis catalysts to form highly functionalised pentacyclic products. The reactions illustrate an interesting difference in reactivity between Grubbs’ catalyst and the second generation catalyst, with the former being more reactive for the early steps of the cascade. Ruthenium based metathesis initiators have been used to convert readily available norbornene derivatives into highly functionalised polycyclic compounds.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2003.09.035