A Remarkably Efficient Phase-Transfer Catalyzed Amination of α-Bromo-α, β-Unsaturated Ketones in Water

A Remarkably Efficient Phase-Transfer Catalyzed Amination of α-Bromo-α, β-Unsaturated Ketones in Water

Tandem conjugate addition–alkylation reaction of various amines with α-bromo-α, β-unsaturated ketones resulted in near-quantitative conversions into the corresponding aziridines when the reaction was carried out in the presence of 10 mol% of phase-transfer, PT catalysts in water. Some chiral quatern...

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Main Authors: Alemayehu Mekonnen, Alemu Tesfaye
Format: Article
Language:English
Published: Hindawi-Wiley 2021-01-01
Series:Heteroatom Chemistry
Online Access:http://dx.doi.org/10.1155/2021/6616458
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spelling doaj-3daf2948125c4f8690e8f821b46312722021-02-15T12:52:42ZengHindawi-WileyHeteroatom Chemistry1042-71631098-10712021-01-01202110.1155/2021/66164586616458A Remarkably Efficient Phase-Transfer Catalyzed Amination of α-Bromo-α, β-Unsaturated Ketones in WaterAlemayehu Mekonnen0Alemu Tesfaye1Department of Chemistry, University of Bahir Dar, P.O. Box 79, Bahir Das, EthiopiaDepartment of Chemistry, University of Bahir Dar, P.O. Box 79, Bahir Das, EthiopiaTandem conjugate addition–alkylation reaction of various amines with α-bromo-α, β-unsaturated ketones resulted in near-quantitative conversions into the corresponding aziridines when the reaction was carried out in the presence of 10 mol% of phase-transfer, PT catalysts in water. Some chiral quaternary ammonium salts derived from Cinchona alkaloids were investigated as water-stable PT catalysts. The scope and limitations of the reaction have also been investigated. The catalytic performances were significantly improved in comparison with the corresponding ordinary quaternary ammonium salt catalysts, and excellent yields (81%–96%) were obtained. Although an increase in the rate of aziridination has been accomplished, no stereoselectivity was observed. The positive values of the protocol have been confirmed.http://dx.doi.org/10.1155/2021/6616458
collection DOAJ
language English
format Article
sources DOAJ
author Alemayehu Mekonnen
Alemu Tesfaye
spellingShingle Alemayehu Mekonnen
Alemu Tesfaye
A Remarkably Efficient Phase-Transfer Catalyzed Amination of α-Bromo-α, β-Unsaturated Ketones in Water
Heteroatom Chemistry
author_facet Alemayehu Mekonnen
Alemu Tesfaye
author_sort Alemayehu Mekonnen
title A Remarkably Efficient Phase-Transfer Catalyzed Amination of α-Bromo-α, β-Unsaturated Ketones in Water
title_short A Remarkably Efficient Phase-Transfer Catalyzed Amination of α-Bromo-α, β-Unsaturated Ketones in Water
title_full A Remarkably Efficient Phase-Transfer Catalyzed Amination of α-Bromo-α, β-Unsaturated Ketones in Water
title_fullStr A Remarkably Efficient Phase-Transfer Catalyzed Amination of α-Bromo-α, β-Unsaturated Ketones in Water
title_full_unstemmed A Remarkably Efficient Phase-Transfer Catalyzed Amination of α-Bromo-α, β-Unsaturated Ketones in Water
title_sort remarkably efficient phase-transfer catalyzed amination of α-bromo-α, β-unsaturated ketones in water
publisher Hindawi-Wiley
series Heteroatom Chemistry
issn 1042-7163
1098-1071
publishDate 2021-01-01
description Tandem conjugate addition–alkylation reaction of various amines with α-bromo-α, β-unsaturated ketones resulted in near-quantitative conversions into the corresponding aziridines when the reaction was carried out in the presence of 10 mol% of phase-transfer, PT catalysts in water. Some chiral quaternary ammonium salts derived from Cinchona alkaloids were investigated as water-stable PT catalysts. The scope and limitations of the reaction have also been investigated. The catalytic performances were significantly improved in comparison with the corresponding ordinary quaternary ammonium salt catalysts, and excellent yields (81%–96%) were obtained. Although an increase in the rate of aziridination has been accomplished, no stereoselectivity was observed. The positive values of the protocol have been confirmed.
url http://dx.doi.org/10.1155/2021/6616458
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AT alemayehumekonnen remarkablyefficientphasetransfercatalyzedaminationofabromoabunsaturatedketonesinwater
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