Hierarchically assembled helicates as reaction platform – from stoichiometric Diels–Alder reactions to enamine catalysis

The stereoselectivity of a Diels–Alder reaction within the periphery of hierarchically assembled titanium(IV) helicates formed from mixtures of achiral, reactive and chiral, unreactive ligands was investigated in detail. Following the pathway of the chiral induction, the chiral ligands, solvents as...

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Autores principales: Van Craen, David, Begall, Jenny, Großkurth, Johannes, Himmel, Leonard, Linnenberg, Oliver, Isaak, Elisabeth, Albrecht, Markus
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2020
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7522461/
https://www.ncbi.nlm.nih.gov/pubmed/33029252
http://dx.doi.org/10.3762/bjoc.16.195
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author Van Craen, David
Begall, Jenny
Großkurth, Johannes
Himmel, Leonard
Linnenberg, Oliver
Isaak, Elisabeth
Albrecht, Markus
author_facet Van Craen, David
Begall, Jenny
Großkurth, Johannes
Himmel, Leonard
Linnenberg, Oliver
Isaak, Elisabeth
Albrecht, Markus
author_sort Van Craen, David
collection PubMed
description The stereoselectivity of a Diels–Alder reaction within the periphery of hierarchically assembled titanium(IV) helicates formed from mixtures of achiral, reactive and chiral, unreactive ligands was investigated in detail. Following the pathway of the chiral induction, the chiral ligands, solvents as well as substituents at the dienophile were carefully varied. Based on the results of the stoichiometric reaction, a secondary amine-catalyzed nitro-Michael reaction is performed as well which afforded reasonable diastereoselectivities.
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spelling pubmed-75224612020-10-06 Hierarchically assembled helicates as reaction platform – from stoichiometric Diels–Alder reactions to enamine catalysis Van Craen, David Begall, Jenny Großkurth, Johannes Himmel, Leonard Linnenberg, Oliver Isaak, Elisabeth Albrecht, Markus Beilstein J Org Chem Full Research Paper The stereoselectivity of a Diels–Alder reaction within the periphery of hierarchically assembled titanium(IV) helicates formed from mixtures of achiral, reactive and chiral, unreactive ligands was investigated in detail. Following the pathway of the chiral induction, the chiral ligands, solvents as well as substituents at the dienophile were carefully varied. Based on the results of the stoichiometric reaction, a secondary amine-catalyzed nitro-Michael reaction is performed as well which afforded reasonable diastereoselectivities. Beilstein-Institut 2020-09-24 /pmc/articles/PMC7522461/ /pubmed/33029252 http://dx.doi.org/10.3762/bjoc.16.195 Text en Copyright © 2020, Van Craen et al. https://creativecommons.org/licenses/by/4.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0). Please note that the reuse, redistribution and reproduction in particular requires that the authors and source are credited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Van Craen, David
Begall, Jenny
Großkurth, Johannes
Himmel, Leonard
Linnenberg, Oliver
Isaak, Elisabeth
Albrecht, Markus
Hierarchically assembled helicates as reaction platform – from stoichiometric Diels–Alder reactions to enamine catalysis
title Hierarchically assembled helicates as reaction platform – from stoichiometric Diels–Alder reactions to enamine catalysis
title_full Hierarchically assembled helicates as reaction platform – from stoichiometric Diels–Alder reactions to enamine catalysis
title_fullStr Hierarchically assembled helicates as reaction platform – from stoichiometric Diels–Alder reactions to enamine catalysis
title_full_unstemmed Hierarchically assembled helicates as reaction platform – from stoichiometric Diels–Alder reactions to enamine catalysis
title_short Hierarchically assembled helicates as reaction platform – from stoichiometric Diels–Alder reactions to enamine catalysis
title_sort hierarchically assembled helicates as reaction platform – from stoichiometric diels–alder reactions to enamine catalysis
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7522461/
https://www.ncbi.nlm.nih.gov/pubmed/33029252
http://dx.doi.org/10.3762/bjoc.16.195
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