Organocatalytic Enantioselective Protonation of Silyl Enolates Mediated by Cinchona Alkaloids and a Latent Source of HF - Normandie Université Access content directly
Journal Articles Angewandte Chemie International Edition Year : 2007

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

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).

Dates and versions

hal-02278779 , version 1 (04-09-2019)

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Cite

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, 2007, 46 (37), pp.7090-7093. ⟨10.1002/anie.200701683⟩. ⟨hal-02278779⟩
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