Enantioselective PCCP Brønsted acid-catalyzed aminalization of aldehydes

Here we present an enantioselective aminalization of aldehydes catalyzed by Brønsted acids based on pentacarboxycyclopentadienes (PCCPs). The cyclization reaction using readily available anthranilamides as building blocks provides access to valuable 2,3-dihydroquinazolinones containing one stereogen...

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Autores principales: Kamlar, Martin, Reiberger, Robert, Nigríni, Martin, Císařová, Ivana, Veselý, Jan
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2021
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8450961/
https://www.ncbi.nlm.nih.gov/pubmed/34621405
http://dx.doi.org/10.3762/bjoc.17.160
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author Kamlar, Martin
Reiberger, Robert
Nigríni, Martin
Císařová, Ivana
Veselý, Jan
author_facet Kamlar, Martin
Reiberger, Robert
Nigríni, Martin
Císařová, Ivana
Veselý, Jan
author_sort Kamlar, Martin
collection PubMed
description Here we present an enantioselective aminalization of aldehydes catalyzed by Brønsted acids based on pentacarboxycyclopentadienes (PCCPs). The cyclization reaction using readily available anthranilamides as building blocks provides access to valuable 2,3-dihydroquinazolinones containing one stereogenic carbon center with good enantioselectivity (ee up to 80%) and excellent yields (up to 97%).
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spelling pubmed-84509612021-10-06 Enantioselective PCCP Brønsted acid-catalyzed aminalization of aldehydes Kamlar, Martin Reiberger, Robert Nigríni, Martin Císařová, Ivana Veselý, Jan Beilstein J Org Chem Full Research Paper Here we present an enantioselective aminalization of aldehydes catalyzed by Brønsted acids based on pentacarboxycyclopentadienes (PCCPs). The cyclization reaction using readily available anthranilamides as building blocks provides access to valuable 2,3-dihydroquinazolinones containing one stereogenic carbon center with good enantioselectivity (ee up to 80%) and excellent yields (up to 97%). Beilstein-Institut 2021-09-16 /pmc/articles/PMC8450961/ /pubmed/34621405 http://dx.doi.org/10.3762/bjoc.17.160 Text en Copyright © 2021, Kamlar et al. https://creativecommons.org/licenses/by/4.0/https://www.beilstein-journals.org/bjoc/terms/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0 (https://creativecommons.org/licenses/by/4.0/) ). Please note that the reuse, redistribution and reproduction in particular requires that the author(s) and source are credited and that individual graphics may be subject to special legal provisions. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms/terms)
spellingShingle Full Research Paper
Kamlar, Martin
Reiberger, Robert
Nigríni, Martin
Císařová, Ivana
Veselý, Jan
Enantioselective PCCP Brønsted acid-catalyzed aminalization of aldehydes
title Enantioselective PCCP Brønsted acid-catalyzed aminalization of aldehydes
title_full Enantioselective PCCP Brønsted acid-catalyzed aminalization of aldehydes
title_fullStr Enantioselective PCCP Brønsted acid-catalyzed aminalization of aldehydes
title_full_unstemmed Enantioselective PCCP Brønsted acid-catalyzed aminalization of aldehydes
title_short Enantioselective PCCP Brønsted acid-catalyzed aminalization of aldehydes
title_sort enantioselective pccp brønsted acid-catalyzed aminalization of aldehydes
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8450961/
https://www.ncbi.nlm.nih.gov/pubmed/34621405
http://dx.doi.org/10.3762/bjoc.17.160
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