Carbenes-catalyzed activation of aldehyde for phenol functionalization
Phthalides are a crucial kind of compounds in both of natural products and pharmaceutical molecules, which exhibit a broad spectrum of biological activities. In particular, 3-Ylidenephthalides represent satisfactory activity on anti-HIV, anti- inflammatory and anti-cancer. Consequently, a numerous o...
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sg-ntu-dr.10356-898692023-02-28T23:40:23Z Carbenes-catalyzed activation of aldehyde for phenol functionalization Song, Runjiang Chi Robin Yonggui School of Physical and Mathematical Sciences DRNTU::Science::Chemistry::Organic chemistry::Organic synthesis Phthalides are a crucial kind of compounds in both of natural products and pharmaceutical molecules, which exhibit a broad spectrum of biological activities. In particular, 3-Ylidenephthalides represent satisfactory activity on anti-HIV, anti- inflammatory and anti-cancer. Consequently, a numerous of literatures have reported the methods to synthesis this series of compounds. However so far, most of these methods need to rely on transition metal catalysts. Besides, the expenses of the metal catalyst and the metal contamination of the product remain to be a pending issue. Herein we report the first example of NHC-catalyzed activation of aldehyde for phenol functionalization, which could consider to be an eco-friendly and highly efficient method for chiral synthesis of phthalide derivatives. My topic will be divided into two parts: Chapter I gives a brief introduction on N-Heterocyclic Carbene in organocatalysis. From it was first separated to it was applied to catalyze various kinds of reaction (Benzoin condensation, Stetter reaction and etc). Followed by its series of extended Breslow intermediates such as homoenolate, acylazolium and azolium enolate. Chapter II introduces our initial attempt on a one-step and enantioselective approach to activate aldehyde for phenol functionalization through using N-Heterocyclic Carbene as the catalyst. Master of Science 2019-02-28T01:02:04Z 2019-12-06T17:35:28Z 2019-02-28T01:02:04Z 2019-12-06T17:35:28Z 2019 Thesis Song, R. (2019). Carbenes-catalyzed activation of aldehyde for phenol functionalization. Master's thesis, Nanyang Technological University, Singapore. https://hdl.handle.net/10356/89869 http://hdl.handle.net/10220/47735 10.32657/10220/47735 en 44 p. application/pdf |
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DRNTU::Science::Chemistry::Organic chemistry::Organic synthesis Song, Runjiang Carbenes-catalyzed activation of aldehyde for phenol functionalization |
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Phthalides are a crucial kind of compounds in both of natural products and pharmaceutical molecules, which exhibit a broad spectrum of biological activities. In particular, 3-Ylidenephthalides represent satisfactory activity on anti-HIV, anti- inflammatory and anti-cancer. Consequently, a numerous of literatures have reported the methods to synthesis this series of compounds. However so far, most of these methods need to rely on transition metal catalysts. Besides, the expenses of the metal catalyst and the metal contamination of the product remain to be a pending issue.
Herein we report the first example of NHC-catalyzed activation of aldehyde for phenol functionalization, which could consider to be an eco-friendly and highly efficient method for chiral synthesis of phthalide derivatives. My topic will be divided into two parts:
Chapter I gives a brief introduction on N-Heterocyclic Carbene in organocatalysis. From it was first separated to it was applied to catalyze various kinds of reaction (Benzoin condensation, Stetter reaction and etc). Followed by its series of extended Breslow intermediates such as homoenolate, acylazolium and azolium enolate.
Chapter II introduces our initial attempt on a one-step and enantioselective approach to activate aldehyde for phenol functionalization through using N-Heterocyclic Carbene as the catalyst. |
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Chi Robin Yonggui |
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Chi Robin Yonggui Song, Runjiang |
format |
Theses and Dissertations |
author |
Song, Runjiang |
author_sort |
Song, Runjiang |
title |
Carbenes-catalyzed activation of aldehyde for phenol functionalization |
title_short |
Carbenes-catalyzed activation of aldehyde for phenol functionalization |
title_full |
Carbenes-catalyzed activation of aldehyde for phenol functionalization |
title_fullStr |
Carbenes-catalyzed activation of aldehyde for phenol functionalization |
title_full_unstemmed |
Carbenes-catalyzed activation of aldehyde for phenol functionalization |
title_sort |
carbenes-catalyzed activation of aldehyde for phenol functionalization |
publishDate |
2019 |
url |
https://hdl.handle.net/10356/89869 http://hdl.handle.net/10220/47735 |
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1759854684246376448 |