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Unique Reactivity of α-Substituted Electron-Deficient Allenes using Sulfinate Salts as Lewis Base Organocatalysts

Abstract : The efficient sulfinate‐catalyzed intermolecular addition reaction of α‐substituted allenyl sulfones and allenoates with Michael acceptors is highlighted. The sequence proceeds under mild conditions to provide a scalable and efficient access to versatile functionalized alkynes, displaying a quaternary stereocentre at the propargylic position. This work enriches the diversity of Lewis base organocatalysts in the field of allene chemistry, in addition to the well‐established phosphine and amine catalysts.
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https://hal-normandie-univ.archives-ouvertes.fr/hal-01830252
Contributor : Jocelyne Levillain <>
Submitted on : Wednesday, July 4, 2018 - 5:54:03 PM
Last modification on : Wednesday, July 1, 2020 - 12:44:30 PM

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Thomas Martzel, Jean-François Lohier, Annie-Claude Gaumont, Jean-François Brière, Stéphane Perrio. Unique Reactivity of α-Substituted Electron-Deficient Allenes using Sulfinate Salts as Lewis Base Organocatalysts. Advanced Synthesis and Catalysis, Wiley-VCH Verlag, 2017, 359 (1), pp.96-106. ⟨10.1002/adsc.201600929⟩. ⟨hal-01830252⟩

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