Synthesis of 1,2,3-triazolium ionic liquid-supported chiral imidazolidinones and their application in asymmetric alkylation reaction

Yunkyung Jeong; Yunjeong Park; Jae Sang Ryu

doi:10.3390/molecules24183349

Synthesis of 1,2,3-triazolium ionic liquid-supported chiral imidazolidinones and their application in asymmetric alkylation reaction

Yunkyung Jeong, Yunjeong Park, Jae Sang Ryu

Department of Pharmaceutical Sciences

Research output: Contribution to journal › Article › peer-review

7 Scopus citations

Abstract

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.

Original language	English
Article number	3349
Journal	Molecules
Volume	24
Issue number	18
DOIs	https://doi.org/10.3390/molecules24183349
State	Published - 14 Sep 2019

Bibliographical note

Funding Information:
Funding: This research was supported by National Research Foundation (NRF) funded by the Korean government (MSIT), the Bio & Medical Technology Development Program (NRF-2017M3A9F5029066) and MRC Program (2018R1A5A2025286).

Publisher Copyright:
© 2019 by the authors.

Keywords

2
3-triazolium; chiral imidazolidinone; asymmetric alkylation; chiral auxiliaries
Ionic liquid; 1

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abstract = "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.",

keywords = "2, 3-triazolium; chiral imidazolidinone; asymmetric alkylation; chiral auxiliaries, Ionic liquid; 1",

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N1 - Funding Information: Funding: This research was supported by National Research Foundation (NRF) funded by the Korean government (MSIT), the Bio & Medical Technology Development Program (NRF-2017M3A9F5029066) and MRC Program (2018R1A5A2025286). Publisher Copyright: © 2019 by the authors.

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N2 - 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.

AB - 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.

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Synthesis of 1,2,3-triazolium ionic liquid-supported chiral imidazolidinones and their application in asymmetric alkylation reaction

Abstract

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Keywords

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