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Stepwise catalytic transformations of renewable feedstock arising from plant oils
Author(s) -
Dupé Antoine,
Le Ravalec Virginie,
Fischmeister Cédric,
Bruneau Christian
Publication year - 2013
Publication title -
european journal of lipid science and technology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.614
H-Index - 94
eISSN - 1438-9312
pISSN - 1438-7697
DOI - 10.1002/ejlt.201200364
Subject(s) - regioselectivity , allylic rearrangement , reactivity (psychology) , chemistry , ruthenium , metathesis , organic chemistry , cycloaddition , nucleophile , catalysis , medicinal chemistry , medicine , polymer , alternative medicine , pathology , polymerization
Two synthetic approaches to produce functionalized plant oil derivatives were investigated. The ruthenium‐catalyzed ene‐yne cross‐metathesis of propargylic carbonates with terminal olefins arising from ethenolysis of methyl oleate provides conjugated dienes. It was shown that the reactivity of these dienes in Diels–Alder [4 + 2]‐cycloaddition with symmetrical electron‐deficient alkynes towards the formation of cyclohexadienes was effective but limited by stereochemical considerations. On the other hand, the stepwise ene‐yne cross‐metathesis followed by ruthenium‐catalyzed nucleophilic allylic substitution by O, N, and C‐nucleophiles was very efficient both in term of reactivity and regioselectivity.