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...
| Main Authors: | , |
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| Other Authors: | |
| Format: | Journal Article |
| Language: | English |
| Published: |
2015
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| Online Access: | https://hdl.handle.net/10356/103510 http://hdl.handle.net/10220/38773 |
| _version_ | 1811695078194806784 |
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| author | Cho, Bokun Wong, Ming Wah |
| author2 | Energy Research Institute @ NTU (ERI@N) |
| author_facet | Energy Research Institute @ NTU (ERI@N) Cho, Bokun Wong, Ming Wah |
| author_sort | Cho, Bokun |
| collection | NTU |
| 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. |
| first_indexed | 2024-10-01T07:17:45Z |
| format | Journal Article |
| id | ntu-10356/103510 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2024-10-01T07:17:45Z |
| publishDate | 2015 |
| record_format | dspace |
| spelling | ntu-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 |
| spellingShingle | 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 bronsted acid activation mode in bicyclic guanidine catalyzed conjugate addition reactions |
| url | https://hdl.handle.net/10356/103510 http://hdl.handle.net/10220/38773 |
| work_keys_str_mv | AT chobokun unconventionalbifunctionallewisbrønstedacidactivationmodeinbicyclicguanidinecatalyzedconjugateadditionreactions AT wongmingwah unconventionalbifunctionallewisbrønstedacidactivationmodeinbicyclicguanidinecatalyzedconjugateadditionreactions |