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Enantioselective 1,3‐Dipolar Cycloaddition of Cyclic Enones Catalyzed by Multifunctional Primary Amines: Beneficial Effects of Hydrogen Bonding
Author(s) -
Chen Wei,
Du Wei,
Duan YongZheng,
Wu Yong,
Yang ShengYong,
Chen YingChun
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.200702618
Subject(s) - enantioselective synthesis , cycloaddition , catalysis , hydrogen bond , chemistry , aryl , combinatorial chemistry , amine gas treating , 1,3 dipolar cycloaddition , organic chemistry , cinchona , primary (astronomy) , hydrogen , alkyl , molecule , physics , astronomy
Hydrogen bonding makes a difference : Multifunctional primary amine catalysts derived from cinchona alkaloids are used in the highly enantioselective 1,3‐dipolar cycloaddition of cyclic enones and azomethine imines (see scheme; R=aryl, alkyl; TIPBA=2,4,6‐triisopropylbenzenesulfonic acid). The synergistic hydrogen‐bonding interaction of catalyst and 1,3‐dipole is essential for stereocontrol.