Organocatalytic Fluorogenic Synthesis of Chromenes

Two fluorescent derivatives of 2-amino-3-carbonitrile-4H-chromene were synthesized by means of a fluorogenic Michael addition of dimedone to dicyano alkene labeled BODIPY derivatives. Different organocatalysts were used in different conditions to obtain compounds 3 and 4 in good yield (up to 65% and...

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Detalles Bibliográficos
Autores principales: Raeisolsadati Oskouei, Mina, Brouwer, Albert M.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Springer US 2017
Materias:
Original Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5393152/
https://www.ncbi.nlm.nih.gov/pubmed/28224357
http://dx.doi.org/10.1007/s10895-017-2049-7
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author Raeisolsadati Oskouei, Mina
Brouwer, Albert M.
author_facet Raeisolsadati Oskouei, Mina
Brouwer, Albert M.
author_sort Raeisolsadati Oskouei, Mina
collection PubMed
description Two fluorescent derivatives of 2-amino-3-carbonitrile-4H-chromene were synthesized by means of a fluorogenic Michael addition of dimedone to dicyano alkene labeled BODIPY derivatives. Different organocatalysts were used in different conditions to obtain compounds 3 and 4 in good yield (up to 65% and 85%) and moderate enantiomeric excess (51% and 41% ee, respectively). This work provides the first example of an enantioselective organocatalytic conversion combined with fluorogenesis. ELECTRONIC SUPPLEMENTARY MATERIAL: The online version of this article (doi:10.1007/s10895-017-2049-7) contains supplementary material, which is available to authorized users.
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spelling pubmed-53931522017-05-02 Organocatalytic Fluorogenic Synthesis of Chromenes Raeisolsadati Oskouei, Mina Brouwer, Albert M. J Fluoresc Original Article Two fluorescent derivatives of 2-amino-3-carbonitrile-4H-chromene were synthesized by means of a fluorogenic Michael addition of dimedone to dicyano alkene labeled BODIPY derivatives. Different organocatalysts were used in different conditions to obtain compounds 3 and 4 in good yield (up to 65% and 85%) and moderate enantiomeric excess (51% and 41% ee, respectively). This work provides the first example of an enantioselective organocatalytic conversion combined with fluorogenesis. ELECTRONIC SUPPLEMENTARY MATERIAL: The online version of this article (doi:10.1007/s10895-017-2049-7) contains supplementary material, which is available to authorized users. Springer US 2017-02-21 2017 /pmc/articles/PMC5393152/ /pubmed/28224357 http://dx.doi.org/10.1007/s10895-017-2049-7 Text en © The Author(s) 2017 Open Access This article is distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution, and reproduction in any medium, provided you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made.
spellingShingle Original Article
Raeisolsadati Oskouei, Mina
Brouwer, Albert M.
Organocatalytic Fluorogenic Synthesis of Chromenes
title Organocatalytic Fluorogenic Synthesis of Chromenes
title_full Organocatalytic Fluorogenic Synthesis of Chromenes
title_fullStr Organocatalytic Fluorogenic Synthesis of Chromenes
title_full_unstemmed Organocatalytic Fluorogenic Synthesis of Chromenes
title_short Organocatalytic Fluorogenic Synthesis of Chromenes
title_sort organocatalytic fluorogenic synthesis of chromenes
topic Original Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5393152/
https://www.ncbi.nlm.nih.gov/pubmed/28224357
http://dx.doi.org/10.1007/s10895-017-2049-7
work_keys_str_mv AT raeisolsadatioskoueimina organocatalyticfluorogenicsynthesisofchromenes
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