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Asymmetric Organocatalytic Protonation of Silyl Enolates Catalyzed by Simple and Original Betaines Derived from Cinchona Alkaloids
Author(s) -
Claraz Aurélie,
Landelle Grégory,
Oudeyer Sylvain,
Levacher Vincent
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201301345
Subject(s) - chemistry , cyclohexanone , cinchona , protonation , cinchona alkaloids , enantioselective synthesis , catalysis , quinidine , silylation , organocatalysis , organic chemistry , betaine , combinatorial chemistry , medicine , ion , pharmacology
The asymmetric protonation of silyl enolates derived from tetralone, benzosuberone, and cyclohexanone has been successfully achieved by using simple and original betaine catalysts derived from Cinchona alkaloids (quinine and quinidine series) to afford the desired α‐substituted ketones in high yields and moderate enantioselectivities. The ease of implementation of this approach along with the easy accessibility of the betaine catalyst (four steps from cheap and commercially available quinine or quinidine) make this approach very appealing for the preparation of enantioenriched α‐monosubstituted carbonyl compounds.