Direct Synthesis of Chiral Porphyrin Macrocyclic Receptors via Regioselective Nitration

[Image: see text] Nitration of tetraphenylporphyrin cage compound 1, at −40 °C, leads to the regioselective formation of the chiral mononitro compound 2 (75% isolated yield) and, at −30 °C, to the achiral syn-dinitro-derivative 3 and the chiral anti-dinitro derivative 4 in a diastereomeric ratio of...

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Autores principales: Varghese, Shaji, Spierenburg, Bram, Swartjes, Anne, White, Paul B., Tinnemans, Paul, Elemans, Johannes A. A. W., Nolte, Roeland J. M.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2018
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6038098/
https://www.ncbi.nlm.nih.gov/pubmed/29894198
http://dx.doi.org/10.1021/acs.orglett.8b01055
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author Varghese, Shaji
Spierenburg, Bram
Swartjes, Anne
White, Paul B.
Tinnemans, Paul
Elemans, Johannes A. A. W.
Nolte, Roeland J. M.
author_facet Varghese, Shaji
Spierenburg, Bram
Swartjes, Anne
White, Paul B.
Tinnemans, Paul
Elemans, Johannes A. A. W.
Nolte, Roeland J. M.
author_sort Varghese, Shaji
collection PubMed
description [Image: see text] Nitration of tetraphenylporphyrin cage compound 1, at −40 °C, leads to the regioselective formation of the chiral mononitro compound 2 (75% isolated yield) and, at −30 °C, to the achiral syn-dinitro-derivative 3 and the chiral anti-dinitro derivative 4 in a diastereomeric ratio of 5:2, which were separated by chromatography (46 and 20% yields, respectively). The structures of the compounds were confirmed by X-ray crystallography.
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spelling pubmed-60380982018-07-15 Direct Synthesis of Chiral Porphyrin Macrocyclic Receptors via Regioselective Nitration Varghese, Shaji Spierenburg, Bram Swartjes, Anne White, Paul B. Tinnemans, Paul Elemans, Johannes A. A. W. Nolte, Roeland J. M. Org Lett [Image: see text] Nitration of tetraphenylporphyrin cage compound 1, at −40 °C, leads to the regioselective formation of the chiral mononitro compound 2 (75% isolated yield) and, at −30 °C, to the achiral syn-dinitro-derivative 3 and the chiral anti-dinitro derivative 4 in a diastereomeric ratio of 5:2, which were separated by chromatography (46 and 20% yields, respectively). The structures of the compounds were confirmed by X-ray crystallography. American Chemical Society 2018-06-12 2018-07-06 /pmc/articles/PMC6038098/ /pubmed/29894198 http://dx.doi.org/10.1021/acs.orglett.8b01055 Text en Copyright © 2018 American Chemical Society This is an open access article published under a Creative Commons Non-Commercial No Derivative Works (CC-BY-NC-ND) Attribution License (http://pubs.acs.org/page/policy/authorchoice_ccbyncnd_termsofuse.html) , which permits copying and redistribution of the article, and creation of adaptations, all for non-commercial purposes.
spellingShingle Varghese, Shaji
Spierenburg, Bram
Swartjes, Anne
White, Paul B.
Tinnemans, Paul
Elemans, Johannes A. A. W.
Nolte, Roeland J. M.
Direct Synthesis of Chiral Porphyrin Macrocyclic Receptors via Regioselective Nitration
title Direct Synthesis of Chiral Porphyrin Macrocyclic Receptors via Regioselective Nitration
title_full Direct Synthesis of Chiral Porphyrin Macrocyclic Receptors via Regioselective Nitration
title_fullStr Direct Synthesis of Chiral Porphyrin Macrocyclic Receptors via Regioselective Nitration
title_full_unstemmed Direct Synthesis of Chiral Porphyrin Macrocyclic Receptors via Regioselective Nitration
title_short Direct Synthesis of Chiral Porphyrin Macrocyclic Receptors via Regioselective Nitration
title_sort direct synthesis of chiral porphyrin macrocyclic receptors via regioselective nitration
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6038098/
https://www.ncbi.nlm.nih.gov/pubmed/29894198
http://dx.doi.org/10.1021/acs.orglett.8b01055
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