Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 7, Pages 2623-2627Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201910399
Keywords
anion binding; chiral macrocycles; cooperative asymmetric catalysis; self-assembly; supramolecular catalysis
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Funding
- National Natural Science Foundation of China [21871276, 21502200, 21521002]
- Chinese Academy of Sciences [QYZDJ-SSW-SLH023]
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An artificial system of substrate-induced dimerization assembly of chiral macrocycle catalysts enables a highly cooperative hydrogen-bonding activation network for efficient enantioselective transformation. These macrocycles contain two thiourea and two chiral diamine moieties and dimerize with sulfate to form a sandwich-like assembly. The macrocycles then adopt an extended conformation and reciprocally complement the hydrogen-bonding interaction sites. Inspired by the guest-induced dynamic assembly, these macrocycles catalyze the decarboxylative Mannich reaction of cyclic aldimines containing a sulfamate heading group. The imine substrate can be activated toward nudeophilic attack of beta-ketoacid by a cooperative hydrogen-bonding network enabled by sulfamate-induced dimerization assembly of the macrocycle catalysts. Highly efficient (> 95 % yield in most cases) and enantioselective (up to 97.5:2.5 er) transformation of a variety of substrates using only 5 mol % macrocycle was achieved.
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