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

Poisson Thomas | Zendy; Dalla Vincent | Zendy; Marsais Francis | Zendy; Dupas Georges | Zendy; Oudeyer Sylvain | Zendy; Levacher Vincent | Zendy

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

Author(s) -

Poisson Thomas,

Dalla Vincent,

Marsais Francis,

Dupas Georges,

Oudeyer Sylvain,

Levacher Vincent

Publication year - 2007

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.200701683

Subject(s) - enantioselective synthesis , cinchona , protonation , silylation , chemistry , cinchona alkaloids , trimethylsilyl , organocatalysis , catalysis , cinchonidine , salt (chemistry) , organic chemistry , combinatorial chemistry , ion

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).

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