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Self‐Assembly of Organocatalysts: Fine‐Tuning Organocatalytic Reactions
Author(s) -
Clarke Matthew L.,
Fuentes José A.
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.200602912
Subject(s) - organocatalysis , catalysis , chemistry , product (mathematics) , michael reaction , proline , enantioselective synthesis , combinatorial chemistry , organic chemistry , biochemistry , mathematics , amino acid , geometry
A cat. with two tales : Hydrogen‐bonding interactions between achiral pyridinone additives and unselective chiral proline‐derived organocatalysts (see picture) result in highly effective catalysts for the Michael addition of nitroalkenes to ketones. In the absence of an additive the reaction is unselective and the product is obtained in about 15 % ee , while the same product is obtained with up to 94 % ee in the presence of an additive.