Unconventional Bifunctional Lewis-Brønsted Acid Activation Mode in Bicyclic Guanidine-Catalyzed Conjugate Addition Reactions

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 a...

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Autores principales: Cho, Bokun, Wong, Ming Wah
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2015
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6331857/
https://www.ncbi.nlm.nih.gov/pubmed/26295222
http://dx.doi.org/10.3390/molecules200815108
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author Cho, Bokun
Wong, Ming Wah
author_facet Cho, Bokun
Wong, Ming Wah
author_sort Cho, Bokun
collection PubMed
description 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(a), while the best electrophiles are flexible 1,4-diamide and 1,4-diester conjugated systems.
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spelling pubmed-63318572019-01-24 Unconventional Bifunctional Lewis-Brønsted Acid Activation Mode in Bicyclic Guanidine-Catalyzed Conjugate Addition Reactions Cho, Bokun Wong, Ming Wah Molecules Article 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(a), while the best electrophiles are flexible 1,4-diamide and 1,4-diester conjugated systems. MDPI 2015-08-18 /pmc/articles/PMC6331857/ /pubmed/26295222 http://dx.doi.org/10.3390/molecules200815108 Text en © 2015 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Cho, Bokun
Wong, Ming Wah
Unconventional Bifunctional Lewis-Brønsted Acid Activation Mode in Bicyclic Guanidine-Catalyzed Conjugate Addition Reactions
title Unconventional Bifunctional Lewis-Brønsted Acid Activation Mode in Bicyclic Guanidine-Catalyzed Conjugate Addition Reactions
title_full Unconventional Bifunctional Lewis-Brønsted Acid Activation Mode in Bicyclic Guanidine-Catalyzed Conjugate Addition Reactions
title_fullStr Unconventional Bifunctional Lewis-Brønsted Acid Activation Mode in Bicyclic Guanidine-Catalyzed Conjugate Addition Reactions
title_full_unstemmed Unconventional Bifunctional Lewis-Brønsted Acid Activation Mode in Bicyclic Guanidine-Catalyzed Conjugate Addition Reactions
title_short Unconventional Bifunctional Lewis-Brønsted Acid Activation Mode in Bicyclic Guanidine-Catalyzed Conjugate Addition Reactions
title_sort unconventional bifunctional lewis-brønsted acid activation mode in bicyclic guanidine-catalyzed conjugate addition reactions
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6331857/
https://www.ncbi.nlm.nih.gov/pubmed/26295222
http://dx.doi.org/10.3390/molecules200815108
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AT wongmingwah unconventionalbifunctionallewisbrønstedacidactivationmodeinbicyclicguanidinecatalyzedconjugateadditionreactions

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