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

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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Main Authors: Cho, Bokun, Wong, Ming Wah
Other Authors: Energy Research Institute @ NTU (ERI@N)
Format: Article
Language:English
Published: 2015
Online Access:https://hdl.handle.net/10356/103510
http://hdl.handle.net/10220/38773
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Institution: Nanyang Technological University
Language: English
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spelling sg-ntu-dr.10356-1035102021-01-20T04:13:07Z Unconventional Bifunctional Lewis-Brønsted Acid Activation Mode in Bicyclic Guanidine-Catalyzed Conjugate Addition Reactions Cho, Bokun Wong, Ming Wah Energy Research Institute @ NTU (ERI@N) 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. Published version 2015-10-01T08:10:09Z 2019-12-06T21:14:14Z 2015-10-01T08:10:09Z 2019-12-06T21:14:14Z 2015 2015 Journal Article 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. 1420-3049 https://hdl.handle.net/10356/103510 http://hdl.handle.net/10220/38773 10.3390/molecules200815108 en Molecules © 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/). application/pdf
institution Nanyang Technological University
building NTU Library
continent Asia
country Singapore
Singapore
content_provider NTU Library
collection DR-NTU
language English
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 pKa, while the best electrophiles are flexible 1,4-diamide and 1,4-diester conjugated systems.
author2 Energy Research Institute @ NTU (ERI@N)
author_facet Energy Research Institute @ NTU (ERI@N)
Cho, Bokun
Wong, Ming Wah
format Article
author Cho, Bokun
Wong, Ming Wah
spellingShingle Cho, Bokun
Wong, Ming Wah
Unconventional Bifunctional Lewis-Brønsted Acid Activation Mode in Bicyclic Guanidine-Catalyzed Conjugate Addition Reactions
author_sort Cho, Bokun
title 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_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_sort unconventional bifunctional lewis-brønsted acid activation mode in bicyclic guanidine-catalyzed conjugate addition reactions
publishDate 2015
url https://hdl.handle.net/10356/103510
http://hdl.handle.net/10220/38773
_version_ 1690658437789122560

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