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2 article(s) from Fischmeister, Cédric

Cross metathesis of unsaturated epoxides for the synthesis of polyfunctional building blocks

Meriem K. Abderrezak,
Kristýna Šichová,
Nancy Dominguez-Boblett,
Antoine Dupé,
Zahia Kabouche,
Christian Bruneau and
Cédric Fischmeister

Beilstein J. Org. Chem. 2015, 11, 1876–1880, doi:10.3762/bjoc.11.201

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Graphical Abstract

Scheme 1: Cross metathesis of 1 with methyl acrylate.

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Scheme 2: Cross metathesis of 1 with acrylonitrile.

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Scheme 3: Tandem cross metathesis/hydrogenation.

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Scheme 4: Trifunctional compounds obtained by ring-opening of epoxide 4.

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Full Research Paper

Published 08 Oct 2015

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Ene–yne cross-metathesis with ruthenium carbene catalysts

Cédric Fischmeister and
Christian Bruneau

Beilstein J. Org. Chem. 2011, 7, 156–166, doi:10.3762/bjoc.7.22

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Scheme 1: Interaction of triple bonds with a metal carbene.

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Scheme 2: General scheme for EYCM and side reactions.

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Figure 1: Selected ruthenium catalysts able to perform EYCM.

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Scheme 3: Catalytic cycle with initial interaction of a metal methylidene with the triple bond.

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Scheme 4: Catalytic cycle with initial interaction of a metal alkylidene with the triple bond.

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Scheme 5: Formation of 2,3-disubstituted dienes via cross-metathesis of alkynes with ethylene.

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Figure 2: Applications of EYCM with ethylene in natural product synthesis.

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Scheme 6: Application of EYCM in sugar chemistry.

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Scheme 7: EYCM as determining step to form vinylcyclopropane derivatives.

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Scheme 8: Sequential EYCM with ethylene/nucleophilic substitution or elimination.

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Scheme 9: Various regioselectivities in EYCM of silylated alkynes.

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Scheme 10: High regio- and stereoselectivities obtained for EYCM with styrenes.

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Scheme 11: EYCM of terminal olefins with internal borylated alkynes.

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Scheme 12: Synthesis of propenylidene cyclobutane via EYCM.

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Scheme 13: Efficient EYCM with vinyl ethers.

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Scheme 14: From cyclopentene to cyclohepta-1,3-dienes via cyclic olefin-alkyne cross-metathesis.

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Scheme 15: Ring expansion via EYCM from bicyclic olefins.

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Scheme 16: Ring contraction resulting from EYCM of cyclooctadiene.

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Scheme 17: Preparation of bicyclic products via diene-alkyne cross-metathesis.

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Scheme 18: Ethylene helping effect in EYCM.

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Scheme 19: Stereoselective EYCM in the presence of ethylene.

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Scheme 20: Sequential ethenolysis/EYCM applied to unsaturated fatty acid esters.

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Scheme 21: Sequential ethenolysis/EYCM applied to symmetrical unsaturated fatty acid derivatives for the produ...

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Published 04 Feb 2011

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