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Organocatalytic Enantioselective Protonation of Silyl Enolates Mediated by Cinchona Alkaloids and a Latent Source of HF

Thomas Poisson 1 Vincent Dalla 2 Francis Marsais 1 Georges Dupas 1 Sylvain Oudeyer 1 Vincent Levacher 1
1 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse
2 URCOM - Unité de Recherche en Chimie Organique et Macromoléculaire
Abstract : Hidden benefits: The enantioselective organocatalytic protonation of silyl enolates has been achieved by using readily available cinchona alkaloid catalysts (1) and a latent source of HF that delivers “at will” the active catalytic hydrogen fluoride salt (1‐HF). This approach leads to enantioselective proton transfer with high enantioselectivities of up to 92 % under mild, neutral, and metal‐free conditions (see scheme, TMS=trimethylsilyl).
Keywords : Alkaloids Enantioselectivity Hydrogen fluoride Ketones Organocatalysis
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https://hal-normandie-univ.archives-ouvertes.fr/hal-02278779
Contributor : Sylvain Oudeyer <>
Submitted on : Wednesday, September 4, 2019 - 3:58:20 PM
Last modification on : Tuesday, November 3, 2020 - 9:50:05 AM

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Thomas Poisson, Vincent Dalla, Francis Marsais, Georges Dupas, Sylvain Oudeyer, et al.. Organocatalytic Enantioselective Protonation of Silyl Enolates Mediated by Cinchona Alkaloids and a Latent Source of HF. Angewandte Chemie International Edition, Wiley-VCH Verlag, 2007, 46 (37), pp.7090-7093. ⟨10.1002/anie.200701683⟩. ⟨hal-02278779⟩

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