Norbornene derivatives bearing endo-substituents in the 5- and 6-positions were studied as substrates for ene-yne metathesis cascades. Substrates which contained an internal alkyne and a terminal alkene or alkyne in each sidechain were found to undergo a metathesis cascade leading to pentacyclic bis-dienes and bis-trienes. Attempts to extend the chemistry further to sidechains containing two internal alkynes or two internal alkynes and a terminal alkene were not successful with the first generation Grubbs' catalyst. However, the substrate containing two internal alkynes did react with the second generation Grubbs' catalyst to give a tetra-diene containing product. Ruthenium based metathesis initiators have been used to convert readily available norbornene derivatives bearing polyunsaturated sidechains into highly functionalised polycyclic compounds. © 2004 Elsevier Ltd. All rights reserved.
Ene-yne metathesis of polyunsaturated norbornene derivatives
Groaz E.;
2004
Abstract
Norbornene derivatives bearing endo-substituents in the 5- and 6-positions were studied as substrates for ene-yne metathesis cascades. Substrates which contained an internal alkyne and a terminal alkene or alkyne in each sidechain were found to undergo a metathesis cascade leading to pentacyclic bis-dienes and bis-trienes. Attempts to extend the chemistry further to sidechains containing two internal alkynes or two internal alkynes and a terminal alkene were not successful with the first generation Grubbs' catalyst. However, the substrate containing two internal alkynes did react with the second generation Grubbs' catalyst to give a tetra-diene containing product. Ruthenium based metathesis initiators have been used to convert readily available norbornene derivatives bearing polyunsaturated sidechains into highly functionalised polycyclic compounds. © 2004 Elsevier Ltd. All rights reserved.Pubblicazioni consigliate
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