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Dynamic One‐Pot Three‐Component Catalytic Asymmetric Transformation by Combination of Hydrogen‐Bond‐Donating and Amine Catalysts
Author(s) -
Lin Shuangzheng,
Deiana Luca,
Zhao GuiLing,
Sun Junliang,
Córdova Armando
Publication year - 2011
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.201101966
Subject(s) - stereocenter , catalysis , amine gas treating , component (thermodynamics) , chemistry , organic chemistry , hydrogen bond , transformation (genetics) , combinatorial chemistry , enantioselective synthesis , molecule , biochemistry , physics , gene , thermodynamics
In control : The first dynamic one‐pot three‐component asymmetric transformation between aldehydes, protected α‐cyanoglycine esters, and enals catalyzed by a combination of a simple hydrogen‐bond‐donating catalyst and a chiral amine catalyst is disclosed. Polysubstituted proline derivatives, which have a quaternary α stereocenter, were synthesized with high endo ‐, diastereo‐, and enantioselectivities (93–99 % ee ).