Enantioselective Synthesis of Highly Substituted Fluoroalkylated Benzopyranones and 3-Coumaranones via N-Heterocyclic Carbene-Catalyzed Intramolecular Annulations

[Image: see text] A highly enantioselective intramolecular NHC-catalyzed approach for the synthesis of fluoroalkylated benzopyranones and 3-coumaranones with all-carbon quaternary stereocenters is presented. This reaction is catalyzed by N-heterocyclic carbenes (NHCs) and involves annulation reactio...

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Autores principales: Barańska, Izabela, Rafińska, Katarzyna, Rafiński, Zbigniew
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10594660/
https://www.ncbi.nlm.nih.gov/pubmed/37793100
http://dx.doi.org/10.1021/acs.joc.3c01099
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author Barańska, Izabela
Rafińska, Katarzyna
Rafiński, Zbigniew
author_facet Barańska, Izabela
Rafińska, Katarzyna
Rafiński, Zbigniew
author_sort Barańska, Izabela
collection PubMed
description [Image: see text] A highly enantioselective intramolecular NHC-catalyzed approach for the synthesis of fluoroalkylated benzopyranones and 3-coumaranones with all-carbon quaternary stereocenters is presented. This reaction is catalyzed by N-heterocyclic carbenes (NHCs) and involves annulation reactions between in situ generated acyl anion intermediates and highly substituted trifluoromethyl-β,β-disubstituted Michael acceptors. The method can also be extended to perfluoroalkyl homologues.
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spelling pubmed-105946602023-10-25 Enantioselective Synthesis of Highly Substituted Fluoroalkylated Benzopyranones and 3-Coumaranones via N-Heterocyclic Carbene-Catalyzed Intramolecular Annulations Barańska, Izabela Rafińska, Katarzyna Rafiński, Zbigniew J Org Chem [Image: see text] A highly enantioselective intramolecular NHC-catalyzed approach for the synthesis of fluoroalkylated benzopyranones and 3-coumaranones with all-carbon quaternary stereocenters is presented. This reaction is catalyzed by N-heterocyclic carbenes (NHCs) and involves annulation reactions between in situ generated acyl anion intermediates and highly substituted trifluoromethyl-β,β-disubstituted Michael acceptors. The method can also be extended to perfluoroalkyl homologues. American Chemical Society 2023-10-04 /pmc/articles/PMC10594660/ /pubmed/37793100 http://dx.doi.org/10.1021/acs.joc.3c01099 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 Barańska, Izabela
Rafińska, Katarzyna
Rafiński, Zbigniew
Enantioselective Synthesis of Highly Substituted Fluoroalkylated Benzopyranones and 3-Coumaranones via N-Heterocyclic Carbene-Catalyzed Intramolecular Annulations
title Enantioselective Synthesis of Highly Substituted Fluoroalkylated Benzopyranones and 3-Coumaranones via N-Heterocyclic Carbene-Catalyzed Intramolecular Annulations
title_full Enantioselective Synthesis of Highly Substituted Fluoroalkylated Benzopyranones and 3-Coumaranones via N-Heterocyclic Carbene-Catalyzed Intramolecular Annulations
title_fullStr Enantioselective Synthesis of Highly Substituted Fluoroalkylated Benzopyranones and 3-Coumaranones via N-Heterocyclic Carbene-Catalyzed Intramolecular Annulations
title_full_unstemmed Enantioselective Synthesis of Highly Substituted Fluoroalkylated Benzopyranones and 3-Coumaranones via N-Heterocyclic Carbene-Catalyzed Intramolecular Annulations
title_short Enantioselective Synthesis of Highly Substituted Fluoroalkylated Benzopyranones and 3-Coumaranones via N-Heterocyclic Carbene-Catalyzed Intramolecular Annulations
title_sort enantioselective synthesis of highly substituted fluoroalkylated benzopyranones and 3-coumaranones via n-heterocyclic carbene-catalyzed intramolecular annulations
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10594660/
https://www.ncbi.nlm.nih.gov/pubmed/37793100
http://dx.doi.org/10.1021/acs.joc.3c01099
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