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2 article(s) from Vrancken, Emmanuel

First DMAP-mediated direct conversion of Morita–Baylis–Hillman alcohols into γ-ketoallylphosphonates: Synthesis of γ-aminoallylphosphonates

Marwa Ayadi,
Haitham Elleuch,
Emmanuel Vrancken and
Farhat Rezgui

Beilstein J. Org. Chem. 2016, 12, 2906–2915, doi:10.3762/bjoc.12.290

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Scheme 1: Synthesis of allylphosphonates from acyclic MBH adducts.

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Scheme 2: Synthesis of γ-ketoallylphosphonates from cyclic MBH adducts.

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Scheme 3: Proposed mechanism for DMAP-mediated direct nucleophilic α-substitution of MBH alcohol 1a.

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Scheme 4: Direct conversion of acyclic MBH alcohols 3a–c into γ-ketoallylphosphonates 4a–f.

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Scheme 5: I₂-Catalyzed direct synthesis of γ-tosylaminophosphonates 6 from alcohol 5.

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Scheme 6: Proposed mechanism for I₂-catalyzed direct nucleophilic substitution of γ-hydroxyallylphosphonate 5...

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Scheme 7: Ce(III)-mediated conversion of acetate 7 into γ-aminophosphonates 8a–d.

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Full Research Paper

Published 30 Dec 2016

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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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