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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).