Synthesis of 1,2,3-Triazolium Ionic Liquid-Supported Chiral Imidazolidinones and Their Application in Asymmetric Alkylation Reaction

Synthesis of 1,2,3-Triazolium Ionic Liquid-Supported Chiral Imidazolidinones and Their Application in Asymmetric Alkylation Reaction

New 1,2,3-triazolium ionic liquid-supported chiral imidazolidinones were developed. The feasibility of the ionic liquid-supported imidazolidinones as chiral auxiliaries was demonstrated in sequential propionylation-alkylation-cleavage reactions, which provided the chiral product with good to excelle...

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Main Authors: Yunkyung Jeong, Yunjeong Park, Jae-Sang Ryu
Format: Article
Language:English
Published: MDPI AG 2019-09-01
Series:Molecules
Subjects:
ionic liquid
1,2,3-triazolium
chiral imidazolidinone
asymmetric alkylation
chiral auxiliaries
Online Access:https://www.mdpi.com/1420-3049/24/18/3349
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spelling doaj-5d4884601b8146f6936a269dc47170162020-11-25T02:03:25ZengMDPI AGMolecules1420-30492019-09-012418334910.3390/molecules24183349molecules24183349Synthesis of 1,2,3-Triazolium Ionic Liquid-Supported Chiral Imidazolidinones and Their Application in Asymmetric Alkylation ReactionYunkyung Jeong0Yunjeong Park1Jae-Sang Ryu2College of Pharmacy & Graduate School of Pharmaceutical Sciences, Ewha Womans University, 52 Ewhayeodae-gil, Seodaemun-Gu, Seoul 03760, KoreaCollege of Pharmacy & Graduate School of Pharmaceutical Sciences, Ewha Womans University, 52 Ewhayeodae-gil, Seodaemun-Gu, Seoul 03760, KoreaCollege of Pharmacy & Graduate School of Pharmaceutical Sciences, Ewha Womans University, 52 Ewhayeodae-gil, Seodaemun-Gu, Seoul 03760, KoreaNew 1,2,3-triazolium ionic liquid-supported chiral imidazolidinones were developed. The feasibility of the ionic liquid-supported imidazolidinones as chiral auxiliaries was demonstrated in sequential propionylation-alkylation-cleavage reactions, which provided the chiral product with good to excellent chemical yields (up to 90%) and high selectivities (up to 94% ee). The progress of the reactions could be monitored by TLC and NMR, and the ionic liquid-supported chiral auxiliaries could be recovered by simple extraction.https://www.mdpi.com/1420-3049/24/18/3349ionic liquid1,2,3-triazoliumchiral imidazolidinoneasymmetric alkylationchiral auxiliaries
collection DOAJ
language English
format Article
sources DOAJ
author Yunkyung Jeong
Yunjeong Park
Jae-Sang Ryu
spellingShingle Yunkyung Jeong
Yunjeong Park
Jae-Sang Ryu
Synthesis of 1,2,3-Triazolium Ionic Liquid-Supported Chiral Imidazolidinones and Their Application in Asymmetric Alkylation Reaction
Molecules
ionic liquid
1,2,3-triazolium
chiral imidazolidinone
asymmetric alkylation
chiral auxiliaries
author_facet Yunkyung Jeong
Yunjeong Park
Jae-Sang Ryu
author_sort Yunkyung Jeong
title Synthesis of 1,2,3-Triazolium Ionic Liquid-Supported Chiral Imidazolidinones and Their Application in Asymmetric Alkylation Reaction
title_short Synthesis of 1,2,3-Triazolium Ionic Liquid-Supported Chiral Imidazolidinones and Their Application in Asymmetric Alkylation Reaction
title_full Synthesis of 1,2,3-Triazolium Ionic Liquid-Supported Chiral Imidazolidinones and Their Application in Asymmetric Alkylation Reaction
title_fullStr Synthesis of 1,2,3-Triazolium Ionic Liquid-Supported Chiral Imidazolidinones and Their Application in Asymmetric Alkylation Reaction
title_full_unstemmed Synthesis of 1,2,3-Triazolium Ionic Liquid-Supported Chiral Imidazolidinones and Their Application in Asymmetric Alkylation Reaction
title_sort synthesis of 1,2,3-triazolium ionic liquid-supported chiral imidazolidinones and their application in asymmetric alkylation reaction
publisher MDPI AG
series Molecules
issn 1420-3049
publishDate 2019-09-01
description New 1,2,3-triazolium ionic liquid-supported chiral imidazolidinones were developed. The feasibility of the ionic liquid-supported imidazolidinones as chiral auxiliaries was demonstrated in sequential propionylation-alkylation-cleavage reactions, which provided the chiral product with good to excellent chemical yields (up to 90%) and high selectivities (up to 94% ee). The progress of the reactions could be monitored by TLC and NMR, and the ionic liquid-supported chiral auxiliaries could be recovered by simple extraction.
topic ionic liquid
1,2,3-triazolium
chiral imidazolidinone
asymmetric alkylation
chiral auxiliaries
url https://www.mdpi.com/1420-3049/24/18/3349
work_keys_str_mv AT yunkyungjeong synthesisof123triazoliumionicliquidsupportedchiralimidazolidinonesandtheirapplicationinasymmetricalkylationreaction
AT yunjeongpark synthesisof123triazoliumionicliquidsupportedchiralimidazolidinonesandtheirapplicationinasymmetricalkylationreaction
AT jaesangryu synthesisof123triazoliumionicliquidsupportedchiralimidazolidinonesandtheirapplicationinasymmetricalkylationreaction
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