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.
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Chen et al. (2007) studied this question.
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