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2 article(s) from Campagne, Jean-Marc

Asymmetric tandem conjugate addition and reaction with carbocations on acylimidazole Michael acceptors

Brigita Mudráková,
Renata Marcia de Figueiredo,
Jean-Marc Campagne and
Radovan Šebesta

Beilstein J. Org. Chem. 2023, 19, 881–888, doi:10.3762/bjoc.19.65

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Scheme 1: Concept of this work.

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Scheme 2: Initial experiments for the trapping of the intermediate enolate Enl-1a with tropylium NTf₂.

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Scheme 3: The reaction scope.

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Figure 1: Comparison of DFT-calculated and experimental ECD of (2R,3R)-4 and (2S,3R)-4.

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Figure 2: DFT calculated (ωB97X-D4/def2-TZVPPD//PBEh-3c/def2-mSVP) HOMO energies and NBO charges for represen...

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Full Research Paper

Published 16 Jun 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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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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Published 28 Jun 2011

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