Synthesis of chiral hydroxyproline based organocatalysts and their applications in Aldol and Michael addition reactions / Noraishah Abdullah

Chiral compounds are common in nature and can have profoundly varied effects in chiral biological systems based on stereochemistry. Organic chemist creates chiral molecules utilizing enantiopure substance, reagent, and catalyst to produce a single enantiomer with ideal pharmacology, toxicity, pharma...

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Main Author:	Abdullah, Noraishah
Format:	Thesis
Language:	English
Published:	2023
Subjects:	QD Chemistry
Online Access:	https://ir.uitm.edu.my/id/eprint/89262/1/89262.pdf
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id	my-uitm-ir.89262
record_format	uketd_dc
spelling	my-uitm-ir.892622024-03-06T01:56:55Z Synthesis of chiral hydroxyproline based organocatalysts and their applications in Aldol and Michael addition reactions / Noraishah Abdullah 2023 Abdullah, Noraishah QD Chemistry Chiral compounds are common in nature and can have profoundly varied effects in chiral biological systems based on stereochemistry. Organic chemist creates chiral molecules utilizing enantiopure substance, reagent, and catalyst to produce a single enantiomer with ideal pharmacology, toxicity, pharmacokinetics, and metabolism properties. This leads to asymmetric reactions using more efficient organocatalysts to prevent waste, increase atom economy, save energy, and increase stereoselectivity. One interesting organocatalyst that is demanded is prolineamide-derived organocatalyst. The first aim of this study is to synthesize prolineamide-derived organocatalyst via 3-hydroxyproline precursor. A new synthetic strategy was developed starting with the Michael addition reaction of glycine ethyl ester, 79 with ethyl acrylate, 78, to give the desired ethyl-3-[(2-ethoxy-2-oxoethyl)amino]propanoate, 80 with an overall yield of 62%. The next strategy was to protect the nitrogen atom with tert-butoxycarbonyl (BOC) using a simple method utilizing NaOH as the base, resulting in 81% yield 2023 Thesis https://ir.uitm.edu.my/id/eprint/89262/ https://ir.uitm.edu.my/id/eprint/89262/1/89262.pdf text en public phd doctoral Universiti Teknologi MARA (UiTM) Faculty of Applied Science Shaameri, Zurina
institution	Universiti Teknologi MARA
collection	UiTM Institutional Repository
language	English
advisor	Shaameri, Zurina
topic	QD Chemistry
spellingShingle	QD Chemistry Abdullah, Noraishah Synthesis of chiral hydroxyproline based organocatalysts and their applications in Aldol and Michael addition reactions / Noraishah Abdullah
description	Chiral compounds are common in nature and can have profoundly varied effects in chiral biological systems based on stereochemistry. Organic chemist creates chiral molecules utilizing enantiopure substance, reagent, and catalyst to produce a single enantiomer with ideal pharmacology, toxicity, pharmacokinetics, and metabolism properties. This leads to asymmetric reactions using more efficient organocatalysts to prevent waste, increase atom economy, save energy, and increase stereoselectivity. One interesting organocatalyst that is demanded is prolineamide-derived organocatalyst. The first aim of this study is to synthesize prolineamide-derived organocatalyst via 3-hydroxyproline precursor. A new synthetic strategy was developed starting with the Michael addition reaction of glycine ethyl ester, 79 with ethyl acrylate, 78, to give the desired ethyl-3-[(2-ethoxy-2-oxoethyl)amino]propanoate, 80 with an overall yield of 62%. The next strategy was to protect the nitrogen atom with tert-butoxycarbonyl (BOC) using a simple method utilizing NaOH as the base, resulting in 81% yield
format	Thesis
qualification_name	Doctor of Philosophy (PhD.)
qualification_level	Doctorate
author	Abdullah, Noraishah
author_facet	Abdullah, Noraishah
author_sort	Abdullah, Noraishah
title	Synthesis of chiral hydroxyproline based organocatalysts and their applications in Aldol and Michael addition reactions / Noraishah Abdullah
title_short	Synthesis of chiral hydroxyproline based organocatalysts and their applications in Aldol and Michael addition reactions / Noraishah Abdullah
title_full	Synthesis of chiral hydroxyproline based organocatalysts and their applications in Aldol and Michael addition reactions / Noraishah Abdullah
title_fullStr	Synthesis of chiral hydroxyproline based organocatalysts and their applications in Aldol and Michael addition reactions / Noraishah Abdullah
title_full_unstemmed	Synthesis of chiral hydroxyproline based organocatalysts and their applications in Aldol and Michael addition reactions / Noraishah Abdullah
title_sort	synthesis of chiral hydroxyproline based organocatalysts and their applications in aldol and michael addition reactions / noraishah abdullah
granting_institution	Universiti Teknologi MARA (UiTM)
granting_department	Faculty of Applied Science
publishDate	2023
url	https://ir.uitm.edu.my/id/eprint/89262/1/89262.pdf
_version_	1794192209422057472

Synthesis of chiral hydroxyproline based organocatalysts and their applications in Aldol and Michael addition reactions / Noraishah Abdullah

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