Next Article in Journal
Porphyrins as Corrosion Inhibitors for N80 Steel in 3.5% NaCl Solution: Electrochemical, Quantum Chemical, QSAR and Monte Carlo Simulations Studies
Next Article in Special Issue
A Mild and Regioselective Ring-Opening of Aziridines with Acid Anhydride Using TBD or PS-TBD as a Catalyst
Previous Article in Journal
Addition of CFCl3 to Aromatic Aldehydes via in Situ Grignard Reaction
Previous Article in Special Issue
Diastereodivergent and Enantioselective [4+2] Annulations of γ-Butenolides with Cyclic 1-Azadienes
Open AccessArticle

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
*
Author to whom correspondence should be addressed.
Present address: Energetic Research Institute, Nanyang Technological University, 50 Nanyang Ave, Singapore 639798, Singapore.
Academic Editor: Choon-Hong Tan
Molecules 2015, 20(8), 15108-15121; https://doi.org/10.3390/molecules200815108
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)
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
Show Figures

Graphical abstract

MDPI and ACS Style

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

Show more citation formats Show less citations formats

Article Access Map by Country/Region

1
Only visits after 24 November 2015 are recorded.
Back to TopTop