Please use this identifier to cite or link to this item: https://doi.org/10.3390/molecules200815108
Title: Unconventional bifunctional Lewis-Brønsted acid activation mode in bicyclic guanidine-catalyzed conjugate addition reactions
Authors: Cho, B
Wong, M.W 
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
Issue Date: 2015
Publisher: MDPI AG
Citation: Cho, B, Wong, M.W (2015). Unconventional bifunctional Lewis-Brønsted acid activation mode in bicyclic guanidine-catalyzed conjugate addition reactions. Molecules 20 (8) : 15108-15121. ScholarBank@NUS Repository. https://doi.org/10.3390/molecules200815108
Rights: Attribution 4.0 International
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 pKa, while the best electrophiles are flexible 1,4-diamide and 1,4-diester conjugated systems. © 2015 by the authors.
Source Title: Molecules
URI: https://scholarbank.nus.edu.sg/handle/10635/179653
ISSN: 1420-3049
DOI: 10.3390/molecules200815108
Rights: Attribution 4.0 International
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