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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...

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Autores principales: Tanaka, Koichi, Kinoshita, Maya, Kayahara, Jun, Uebayashi, Yutaro, Nakaji, Kazusada, Morawiak, Maja, Urbanczyk-Lipkowska, Zofia
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2018
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.
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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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