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Molecules 2015, 20(8), 15108-15121; doi:10.3390/molecules200815108

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

Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543, Singapore
Present address: Energetic Research Institute, Nanyang Technological University, 50 Nanyang Ave, Singapore 639798, Singapore.
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Author to whom correspondence should be addressed.
Academic Editor: Choon-Hong Tan
Received: 3 June 2015 / Revised: 3 June 2015 / Accepted: 10 August 2015 / Published: 18 August 2015
(This article belongs to the Special Issue Brønsted Base Catalysis in Organic Synthesis)
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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. View Full-Text
Keywords: organocatalysis; activation mode; guanidine; bifunctional activation; mechanism; DFT calculations organocatalysis; activation mode; guanidine; bifunctional activation; mechanism; DFT calculations
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Cho, B.; Wong, M.W. Unconventional Bifunctional Lewis-Brønsted Acid Activation Mode in Bicyclic Guanidine-Catalyzed Conjugate Addition Reactions. Molecules 2015, 20, 15108-15121.

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