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Process Intensification of Asymmetri...

Qian, Ng Xiao,

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Process Intensification of Asymmetric Catalytic Reactions and the Incorporation to Drug Synthesis /

Record Type:	Electronic resources : Monograph/item
Title/Author:	Process Intensification of Asymmetric Catalytic Reactions and the Incorporation to Drug Synthesis // Ng Xiao Qian.
Author:	Qian, Ng Xiao,
Description:	1 electronic resource (237 pages)
Notes:	Source: Dissertations Abstracts International, Volume: 86-06, Section: B.
Contained By:	Dissertations Abstracts International86-06B.
Subject:	Polymers. -
Online resource:	https://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=31777242
ISBN:	9798346772965

Process Intensification of Asymmetric Catalytic Reactions and the Incorporation to Drug Synthesis /
Qian, Ng Xiao,

Process Intensification of Asymmetric Catalytic Reactions and the Incorporation to Drug Synthesis /Ng Xiao Qian. - 1 electronic resource (237 pages)

Source: Dissertations Abstracts International, Volume: 86-06, Section: B.

This thesis details 5 chapters describing the introduction and application of process intensification to methodologies and reaction development. The first an introductory chapter, while the subsequent two chapters detail asymmetric catalytic reactions. Chapter 4 illustrates the large-scale synthesis of commercial drugs using borrowing hydrogen reactions, and the last chapter describes a preliminary work that attempted the borrowing hydrogen and synthesis of amines using electrochemistry.The first chapter the introduction, details various strategies for the immobilization of organocatalysts, scale-up and the process intensification of reactions. Various amination strategies, including borrowing hydrogen amination would also be discussed in detail, while highlighting the importance of amination in drug synthesis.The second chapter describes performing process intensification on our group's previously developed allylsilylation reaction using cinchona alkaloid amide catalyst. Previously, recovery of catalyst would require the use of column chromatography which is laborious and unsustainable. As such, we developed an immobilized cinchona alkaloid catalyst that allows easy recovery of catalyst while preserving the enantiomeric excess in the product. In addition, the synthesis of the catalyst was improved, allowing toxic chlorinating agents to be avoided and reaction to be performed under aqueous conditions.In chapter 3, we present the first asymmetric borrowing hydrogen synthesis of aliphatic amines. Using the cooperative catalysis of a chiral iridium complex with a chiral phosphoric acid, we managed to access a wide range of 2 aliphatic amines from their respective feedstock alcohols with good yields and enantioselectivity. We have also discovered an intriguing racemization mechanism of enantioenriched amine products, which could influence reaction optimization in similar reactions.The next chapter is then a continuation of the same methodology, but with application of process intensification principles. Using such process intensified borrowing hydrogen methodology, we managed to synthesize commercial drugs with good yields, and comparable cost to the patented methods. Using our methodology, there are advantages such as the use of more sustainable reagents, better productivity, and lowered PMI values. In addition, despite using iridium catalysts, we were able to reduce the final iridium content in final product to acceptable ranges using a simple precipitation process.Lastly, preliminary work on the attempted synthesis of amines and borrowing hydrogen using electrochemistry will be discussed. Using strategies referenced from other groups, we were able to reduce benzyl imines to their respective imines using a sacrificial magnesium anode. However, further work to introduce enantioselectivity or simultaneous oxidation of alcohols into aldehydes proved to be challenging. More investigation into this research direction is currently ongoing in our group.

English

ISBN: 9798346772965Subjects--Topical Terms:

535398
Polymers.

Process Intensification of Asymmetric Catalytic Reactions and the Incorporation to Drug Synthesis /
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520 $a This thesis details 5 chapters describing the introduction and application of process intensification to methodologies and reaction development. The first an introductory chapter, while the subsequent two chapters detail asymmetric catalytic reactions. Chapter 4 illustrates the large-scale synthesis of commercial drugs using borrowing hydrogen reactions, and the last chapter describes a preliminary work that attempted the borrowing hydrogen and synthesis of amines using electrochemistry.The first chapter the introduction, details various strategies for the immobilization of organocatalysts, scale-up and the process intensification of reactions. Various amination strategies, including borrowing hydrogen amination would also be discussed in detail, while highlighting the importance of amination in drug synthesis.The second chapter describes performing process intensification on our group's previously developed allylsilylation reaction using cinchona alkaloid amide catalyst. Previously, recovery of catalyst would require the use of column chromatography which is laborious and unsustainable. As such, we developed an immobilized cinchona alkaloid catalyst that allows easy recovery of catalyst while preserving the enantiomeric excess in the product. In addition, the synthesis of the catalyst was improved, allowing toxic chlorinating agents to be avoided and reaction to be performed under aqueous conditions.In chapter 3, we present the first asymmetric borrowing hydrogen synthesis of aliphatic amines. Using the cooperative catalysis of a chiral iridium complex with a chiral phosphoric acid, we managed to access a wide range of 2 aliphatic amines from their respective feedstock alcohols with good yields and enantioselectivity. We have also discovered an intriguing racemization mechanism of enantioenriched amine products, which could influence reaction optimization in similar reactions.The next chapter is then a continuation of the same methodology, but with application of process intensification principles. Using such process intensified borrowing hydrogen methodology, we managed to synthesize commercial drugs with good yields, and comparable cost to the patented methods. Using our methodology, there are advantages such as the use of more sustainable reagents, better productivity, and lowered PMI values. In addition, despite using iridium catalysts, we were able to reduce the final iridium content in final product to acceptable ranges using a simple precipitation process.Lastly, preliminary work on the attempted synthesis of amines and borrowing hydrogen using electrochemistry will be discussed. Using strategies referenced from other groups, we were able to reduce benzyl imines to their respective imines using a sacrificial magnesium anode. However, further work to introduce enantioselectivity or simultaneous oxidation of alcohols into aldehydes proved to be challenging. More investigation into this research direction is currently ongoing in our group.
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