Cu (II)-Catalyzed Asymmetric Henry Reaction with a Novel C(1)-Symmetric Aminopinane-Derived Ligand

A novel C(1)-symmetric dinitrogen ligand was synthesized in high yield from commercially available (1R,2R,3R,5S)-(−)-isopinocampheylamine and 1-methyl-2-imidazolecarboxaldehyde. In combination with Cu(OAc)(2)∙H(2)O, this new ligand promote the reaction between nitromethane and aliphatic aldehydes wi...

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Detalles Bibliográficos
Autores principales: Filippova, Liudmila, Stenstrøm, Yngve, Hansen, Trond Vidar
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2015
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6272271/
https://www.ncbi.nlm.nih.gov/pubmed/25859780
http://dx.doi.org/10.3390/molecules20046224
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author Filippova, Liudmila
Stenstrøm, Yngve
Hansen, Trond Vidar
author_facet Filippova, Liudmila
Stenstrøm, Yngve
Hansen, Trond Vidar
author_sort Filippova, Liudmila
collection PubMed
description A novel C(1)-symmetric dinitrogen ligand was synthesized in high yield from commercially available (1R,2R,3R,5S)-(−)-isopinocampheylamine and 1-methyl-2-imidazolecarboxaldehyde. In combination with Cu(OAc)(2)∙H(2)O, this new ligand promote the reaction between nitromethane and aliphatic aldehydes with high yields (up to 97%) and moderate enantioselectivities (up to 67% ee). The reactions with benzaldehyde required prolonged reaction time that resulted in diminished yields, but accompanied with ee-values in the 55%–76% range.
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spelling pubmed-62722712018-12-03 Cu (II)-Catalyzed Asymmetric Henry Reaction with a Novel C(1)-Symmetric Aminopinane-Derived Ligand Filippova, Liudmila Stenstrøm, Yngve Hansen, Trond Vidar Molecules Article A novel C(1)-symmetric dinitrogen ligand was synthesized in high yield from commercially available (1R,2R,3R,5S)-(−)-isopinocampheylamine and 1-methyl-2-imidazolecarboxaldehyde. In combination with Cu(OAc)(2)∙H(2)O, this new ligand promote the reaction between nitromethane and aliphatic aldehydes with high yields (up to 97%) and moderate enantioselectivities (up to 67% ee). The reactions with benzaldehyde required prolonged reaction time that resulted in diminished yields, but accompanied with ee-values in the 55%–76% range. MDPI 2015-04-09 /pmc/articles/PMC6272271/ /pubmed/25859780 http://dx.doi.org/10.3390/molecules20046224 Text en © 2015 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Filippova, Liudmila
Stenstrøm, Yngve
Hansen, Trond Vidar
Cu (II)-Catalyzed Asymmetric Henry Reaction with a Novel C(1)-Symmetric Aminopinane-Derived Ligand
title Cu (II)-Catalyzed Asymmetric Henry Reaction with a Novel C(1)-Symmetric Aminopinane-Derived Ligand
title_full Cu (II)-Catalyzed Asymmetric Henry Reaction with a Novel C(1)-Symmetric Aminopinane-Derived Ligand
title_fullStr Cu (II)-Catalyzed Asymmetric Henry Reaction with a Novel C(1)-Symmetric Aminopinane-Derived Ligand
title_full_unstemmed Cu (II)-Catalyzed Asymmetric Henry Reaction with a Novel C(1)-Symmetric Aminopinane-Derived Ligand
title_short Cu (II)-Catalyzed Asymmetric Henry Reaction with a Novel C(1)-Symmetric Aminopinane-Derived Ligand
title_sort cu (ii)-catalyzed asymmetric henry reaction with a novel c(1)-symmetric aminopinane-derived ligand
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6272271/
https://www.ncbi.nlm.nih.gov/pubmed/25859780
http://dx.doi.org/10.3390/molecules20046224
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