Unconventional bifunctional Lewis-Brønsted acid activation mode in bicyclic guanidine-catalyzed conjugate addition reactions
Cho, B Wong, M.W
Cho, B
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Alternative Title
Abstract
DFT calculations have demonstrated that the unconventional bifunctional Brønsted-Lewis acid activation mode is generally applicable to a range of nucleophilic conjugate additions catalyzed by bicyclic guanidine catalysts. It competes readily with the conventional bifunctional Brønsted acid mode of activation. The optimal pro-nucleophiles for this unconventional bifunctional activation are acidic substrates with low pK<inf>a</inf>, while the best electrophiles are flexible 1,4-diamide and 1,4-diester conjugated systems. © 2015 by the authors.
Keywords
fused heterocyclic rings, guanidine, Lewis acid, phenol derivative, phthalimide derivative, thiol derivative, thiophenol, catalysis, chemical structure, chemistry, conformation, organic chemistry, procedures, Bicyclo Compounds, Heterocyclic, Catalysis, Chemistry, Organic, Guanidine, Lewis Acids, Models, Molecular, Molecular Conformation, Phenols, Phthalimides, Sulfhydryl Compounds
Source Title
Molecules
Publisher
MDPI AG
Series/Report No.
Collections
Rights
Attribution 4.0 International
Date
2015
DOI
10.3390/molecules200815108
Type
Article