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2 article(s) from Gayon, Eric

Total synthesis of insect sex pheromones: recent improvements based on iron-mediated cross-coupling chemistry

Eric Gayon,
Guillaume Lefèvre,
Olivier Guerret,
Adrien Tintar and
Pablo Chourreu

Beilstein J. Org. Chem. 2023, 19, 158–166, doi:10.3762/bjoc.19.15

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Scheme 1: Structure of the (8E,10Z)-tetradecadienal (1, sex pheromone of the horse-chestnut leaf miner) and r...

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Scheme 2: a) Alkyl–vinyl seminal cross-coupling reaction by Kochi; b) improved procedure described by Cahiez.

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Scheme 3: Iron-catalyzed cross-coupling of n-OctMgCl with a 1-butadienyl phosphate.

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Scheme 4: Synthesis of several insect sex pheromones (a) red bollworm moth, b) European grapevine moth, c) ho...

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Scheme 5: Cross-coupling of alkyl Grignard reagents with a) alkenyl or b) aryl halides involving EtOMgCl as a...

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Scheme 6: Total synthesis of codling moth sex pheromone 4 using an iron-mediated cross-coupling between an α,...

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Album

Perspective

Published 14 Feb 2023

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Gold-catalyzed propargylic substitutions: Scope and synthetic developments

Olivier Debleds,
Eric Gayon,
Emmanuel Vrancken and
Jean-Marc Campagne

Beilstein J. Org. Chem. 2011, 7, 866–877, doi:10.3762/bjoc.7.99

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Graphical Abstract

Scheme 1: Gold-catalyzed propargylic substitutions.

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Scheme 2: Propargylic substitution: scope of substrates.

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Scheme 3: Propargylic substitutions on allylic/propargylic substrates.

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Scheme 4: Direct propargylic substitutions: Scope of nucleophiles.

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Scheme 5: Meyer–Schuster rearrangements.

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Scheme 6: Silyl-protected propargyl alcohols in propargylic substitutions.

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Scheme 7: Acetylacetone as nucleophile in direct propargylic substitution.

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Scheme 8: Enantiomerically enriched propargylic alcohols.

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Scheme 9: Scope of ‘activated’ alcohols in direct substitution reactions.

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Scheme 10: BF₃ vs AuCl₃ in propargylic substitutions [25].

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Scheme 11: The use of bis-nucleophiles in direct propargylic substitutions.

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Scheme 12: Tandem reactions from protected hydroxylamines and propargylic alcohols. P = Cbz, PhSO₂.

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Scheme 13: Tentative hydrolysis of bis-adduct 24a.

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Scheme 14: Iron-catalyzed propargylic substitutions.

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Scheme 15: Isoxazolines formation.

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Scheme 16: Addition of nucleophiles to isoxazolines.

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Scheme 17: Potential mechanistic pathways.

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Scheme 18: Synthesis of furans from homoproargylic alcohols.

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Scheme 19: Synthesis of furans.

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Scheme 20: Propargylic substitutions: Synthetic applications. GH2 = Grubbs–Hoveyda 2^nd generation catalyst.

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Album

Review

Published 28 Jun 2011

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