Kinetic Resolution of Allyltriflamides through a Pd-Catalyzed C–H Functionalization with Allenes: Asymmetric Assembly of Tetrahydropyridines

[Image: see text] Enantioenriched, six-membered azacycles are essential structural motifs in many products of pharmaceutical or agrochemical interest. Here we report a simple and practical method for enantioselective assembly of tetrahydropyridines, which is paired to a kinetic resolution of α-branc...

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Autores principales: González, José Manuel, Cendón, Borja, Mascareñas, José Luis, Gulías, Moisés
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8459456/
https://www.ncbi.nlm.nih.gov/pubmed/33651598
http://dx.doi.org/10.1021/jacs.1c01929
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author González, José Manuel
Cendón, Borja
Mascareñas, José Luis
Gulías, Moisés
author_facet González, José Manuel
Cendón, Borja
Mascareñas, José Luis
Gulías, Moisés
author_sort González, José Manuel
collection PubMed
description [Image: see text] Enantioenriched, six-membered azacycles are essential structural motifs in many products of pharmaceutical or agrochemical interest. Here we report a simple and practical method for enantioselective assembly of tetrahydropyridines, which is paired to a kinetic resolution of α-branched allyltriflamides. The reaction consists of a formal (4+2) cycloaddition between the allylamine derivatives and allenes and is initiated by a palladium(II)-catalyzed C–H activation process. Both the chiral allylamide precursors and the tetrahydropyridine adducts were successfully obtained in high yields, with excellent enantioselectivity (up to 99% ee) and selectivity values of up to 127.
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spelling pubmed-84594562021-09-24 Kinetic Resolution of Allyltriflamides through a Pd-Catalyzed C–H Functionalization with Allenes: Asymmetric Assembly of Tetrahydropyridines González, José Manuel Cendón, Borja Mascareñas, José Luis Gulías, Moisés J Am Chem Soc [Image: see text] Enantioenriched, six-membered azacycles are essential structural motifs in many products of pharmaceutical or agrochemical interest. Here we report a simple and practical method for enantioselective assembly of tetrahydropyridines, which is paired to a kinetic resolution of α-branched allyltriflamides. The reaction consists of a formal (4+2) cycloaddition between the allylamine derivatives and allenes and is initiated by a palladium(II)-catalyzed C–H activation process. Both the chiral allylamide precursors and the tetrahydropyridine adducts were successfully obtained in high yields, with excellent enantioselectivity (up to 99% ee) and selectivity values of up to 127. American Chemical Society 2021-03-02 2021-03-17 /pmc/articles/PMC8459456/ /pubmed/33651598 http://dx.doi.org/10.1021/jacs.1c01929 Text en © 2021 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 González, José Manuel
Cendón, Borja
Mascareñas, José Luis
Gulías, Moisés
Kinetic Resolution of Allyltriflamides through a Pd-Catalyzed C–H Functionalization with Allenes: Asymmetric Assembly of Tetrahydropyridines
title Kinetic Resolution of Allyltriflamides through a Pd-Catalyzed C–H Functionalization with Allenes: Asymmetric Assembly of Tetrahydropyridines
title_full Kinetic Resolution of Allyltriflamides through a Pd-Catalyzed C–H Functionalization with Allenes: Asymmetric Assembly of Tetrahydropyridines
title_fullStr Kinetic Resolution of Allyltriflamides through a Pd-Catalyzed C–H Functionalization with Allenes: Asymmetric Assembly of Tetrahydropyridines
title_full_unstemmed Kinetic Resolution of Allyltriflamides through a Pd-Catalyzed C–H Functionalization with Allenes: Asymmetric Assembly of Tetrahydropyridines
title_short Kinetic Resolution of Allyltriflamides through a Pd-Catalyzed C–H Functionalization with Allenes: Asymmetric Assembly of Tetrahydropyridines
title_sort kinetic resolution of allyltriflamides through a pd-catalyzed c–h functionalization with allenes: asymmetric assembly of tetrahydropyridines
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8459456/
https://www.ncbi.nlm.nih.gov/pubmed/33651598
http://dx.doi.org/10.1021/jacs.1c01929
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