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Cupreines and Cupreidines: An Emerging Class of Bifunctional Cinchona Organocatalysts
Author(s) -
Marcelli Tommaso,
van Maarseveen Jan H.,
Hiemstra Henk
Publication year - 2006
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.200602318
Subject(s) - bifunctional , organocatalysis , cinchona alkaloids , cinchona , chemistry , catalysis , scope (computer science) , hydrogen bond , stereoselectivity , combinatorial chemistry , organic chemistry , enantioselective synthesis , computer science , molecule , programming language
In the steadily expanding field of organocatalysis, cinchona alkaloids play a prominent role. Until the late 1990s, bifunctional catalysts based on this scaffold relied exclusively on the C9‐hydroxy group as the hydrogen‐bond donor. Recently, new cinchona catalysts have been developed that feature a phenolic OH group in the C6′ position—a structural feature that allows a diverse set of reactions to be catalyzed in a highly stereoselective fashion. This Minireview describes the scope and modes of action of this new class of asymmetric bifunctional organocatalysts.