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

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: Organocatalysis; Ketones; Hydrogen fluoride; Enantioselectivity; Alkaloids

Domains: Chemical Sciences; Organic chemistry

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⟩