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Asymmetric ring-opening reaction of meso-epoxides with aromatic amines using homochiral metal–organic frameworks as recyclable heterogeneous catalysts
An efficient asymmetric ring-opening (ARO) reaction of meso-epoxides with aromatic amines catalysed by a series of homochiral metal–organic frameworks (MOFs) was carried out. Excellent results (up to 95% ee) for the ARO of cyclohexene oxide with several aromatic amines were achieved with a homochira...
Autores principales: | , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
The Royal Society of Chemistry
2018
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9083937/ https://www.ncbi.nlm.nih.gov/pubmed/35542745 http://dx.doi.org/10.1039/c8ra05163a |
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author | Tanaka, Koichi Kinoshita, Maya Kayahara, Jun Uebayashi, Yutaro Nakaji, Kazusada Morawiak, Maja Urbanczyk-Lipkowska, Zofia |
author_facet | Tanaka, Koichi Kinoshita, Maya Kayahara, Jun Uebayashi, Yutaro Nakaji, Kazusada Morawiak, Maja Urbanczyk-Lipkowska, Zofia |
author_sort | Tanaka, Koichi |
collection | PubMed |
description | An efficient asymmetric ring-opening (ARO) reaction of meso-epoxides with aromatic amines catalysed by a series of homochiral metal–organic frameworks (MOFs) was carried out. Excellent results (up to 95% ee) for the ARO of cyclohexene oxide with several aromatic amines were achieved with a homochiral MOF derived from the ligand (R)-2,2′-dihydroxyl-1,1′-binaphthalene-5,5′-dicarboxylic acid. Furthermore, homochiral MOFs based on (R)-2,2′-dihydroxy-1,1′-binaphthyl-4,4′-di(4-benzoic acid) and (R)-2,2′-diethoxy-1,1′-binaphthyl-4,4′-di(5-isophthalic acid) catalysed ARO reactions of cis-stilbene oxide with 1-naphthylamine in high yield (up to 95%) and excellent enantioselectivity (up to 97%) of the β-amino alcohol. The MOF catalysts were recoverable and recyclable with retention of their performance. |
format | Online Article Text |
id | pubmed-9083937 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2018 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-90839372022-05-09 Asymmetric ring-opening reaction of meso-epoxides with aromatic amines using homochiral metal–organic frameworks as recyclable heterogeneous catalysts Tanaka, Koichi Kinoshita, Maya Kayahara, Jun Uebayashi, Yutaro Nakaji, Kazusada Morawiak, Maja Urbanczyk-Lipkowska, Zofia RSC Adv Chemistry An efficient asymmetric ring-opening (ARO) reaction of meso-epoxides with aromatic amines catalysed by a series of homochiral metal–organic frameworks (MOFs) was carried out. Excellent results (up to 95% ee) for the ARO of cyclohexene oxide with several aromatic amines were achieved with a homochiral MOF derived from the ligand (R)-2,2′-dihydroxyl-1,1′-binaphthalene-5,5′-dicarboxylic acid. Furthermore, homochiral MOFs based on (R)-2,2′-dihydroxy-1,1′-binaphthyl-4,4′-di(4-benzoic acid) and (R)-2,2′-diethoxy-1,1′-binaphthyl-4,4′-di(5-isophthalic acid) catalysed ARO reactions of cis-stilbene oxide with 1-naphthylamine in high yield (up to 95%) and excellent enantioselectivity (up to 97%) of the β-amino alcohol. The MOF catalysts were recoverable and recyclable with retention of their performance. The Royal Society of Chemistry 2018-08-06 /pmc/articles/PMC9083937/ /pubmed/35542745 http://dx.doi.org/10.1039/c8ra05163a Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/ |
spellingShingle | Chemistry Tanaka, Koichi Kinoshita, Maya Kayahara, Jun Uebayashi, Yutaro Nakaji, Kazusada Morawiak, Maja Urbanczyk-Lipkowska, Zofia Asymmetric ring-opening reaction of meso-epoxides with aromatic amines using homochiral metal–organic frameworks as recyclable heterogeneous catalysts |
title | Asymmetric ring-opening reaction of meso-epoxides with aromatic amines using homochiral metal–organic frameworks as recyclable heterogeneous catalysts |
title_full | Asymmetric ring-opening reaction of meso-epoxides with aromatic amines using homochiral metal–organic frameworks as recyclable heterogeneous catalysts |
title_fullStr | Asymmetric ring-opening reaction of meso-epoxides with aromatic amines using homochiral metal–organic frameworks as recyclable heterogeneous catalysts |
title_full_unstemmed | Asymmetric ring-opening reaction of meso-epoxides with aromatic amines using homochiral metal–organic frameworks as recyclable heterogeneous catalysts |
title_short | Asymmetric ring-opening reaction of meso-epoxides with aromatic amines using homochiral metal–organic frameworks as recyclable heterogeneous catalysts |
title_sort | asymmetric ring-opening reaction of meso-epoxides with aromatic amines using homochiral metal–organic frameworks as recyclable heterogeneous catalysts |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9083937/ https://www.ncbi.nlm.nih.gov/pubmed/35542745 http://dx.doi.org/10.1039/c8ra05163a |
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