Enantioselective Allylation of Stereogenic Nitrogen Centers

[Image: see text] Most tertiary amines with a stereogenic nitrogen center undergo rapid racemization at room temperature. Consequently, the quaternization of amines under dynamic kinetic resolution seems feasible. N-Methyl tetrahydroisoquinolines are converted into configurationally stable ammonium...

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Autores principales: Zaitseva, Snizhana, Prescimone, Alessandro, Köhler, Valentin
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10028698/
https://www.ncbi.nlm.nih.gov/pubmed/36881477
http://dx.doi.org/10.1021/acs.orglett.3c00195
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author Zaitseva, Snizhana
Prescimone, Alessandro
Köhler, Valentin
author_facet Zaitseva, Snizhana
Prescimone, Alessandro
Köhler, Valentin
author_sort Zaitseva, Snizhana
collection PubMed
description [Image: see text] Most tertiary amines with a stereogenic nitrogen center undergo rapid racemization at room temperature. Consequently, the quaternization of amines under dynamic kinetic resolution seems feasible. N-Methyl tetrahydroisoquinolines are converted into configurationally stable ammonium ions by Pd-catalyzed allylic alkylation. The optimization of conditions and the evaluation of the substrate scope enabled high conversions and an enantiomeric ratio of up to 10:90. We report here the first examples for the enantioselective catalytic synthesis of chiral ammonium ions.
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spelling pubmed-100286982023-03-22 Enantioselective Allylation of Stereogenic Nitrogen Centers Zaitseva, Snizhana Prescimone, Alessandro Köhler, Valentin Org Lett [Image: see text] Most tertiary amines with a stereogenic nitrogen center undergo rapid racemization at room temperature. Consequently, the quaternization of amines under dynamic kinetic resolution seems feasible. N-Methyl tetrahydroisoquinolines are converted into configurationally stable ammonium ions by Pd-catalyzed allylic alkylation. The optimization of conditions and the evaluation of the substrate scope enabled high conversions and an enantiomeric ratio of up to 10:90. We report here the first examples for the enantioselective catalytic synthesis of chiral ammonium ions. American Chemical Society 2023-03-07 /pmc/articles/PMC10028698/ /pubmed/36881477 http://dx.doi.org/10.1021/acs.orglett.3c00195 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Zaitseva, Snizhana
Prescimone, Alessandro
Köhler, Valentin
Enantioselective Allylation of Stereogenic Nitrogen Centers
title Enantioselective Allylation of Stereogenic Nitrogen Centers
title_full Enantioselective Allylation of Stereogenic Nitrogen Centers
title_fullStr Enantioselective Allylation of Stereogenic Nitrogen Centers
title_full_unstemmed Enantioselective Allylation of Stereogenic Nitrogen Centers
title_short Enantioselective Allylation of Stereogenic Nitrogen Centers
title_sort enantioselective allylation of stereogenic nitrogen centers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10028698/
https://www.ncbi.nlm.nih.gov/pubmed/36881477
http://dx.doi.org/10.1021/acs.orglett.3c00195
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