Palladium-Catalyzed, Enantioselective Formal Cycloaddition between Benzyltriflamides and Allenes: Straightforward Access to Enantioenriched Isoquinolines

[Image: see text] Benzyl and allyltriflamides can engage in Pd-catalyzed oxidative (4+2) annulations with allenes, to produce highly valuable tetrahydroisoquinoline or dihydropyridine skeletons. The reaction is especially efficient when carried out in the presence of designed N-protected amino acids...

Descripción completa

Detalles Bibliográficos
Autores principales: Vidal, Xandro, Mascareñas, José L., Gulías, Moisés
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2019
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6497426/
https://www.ncbi.nlm.nih.gov/pubmed/30636417
http://dx.doi.org/10.1021/jacs.8b12636
_version_ 1783415468990660608
author Vidal, Xandro
Mascareñas, José L.
Gulías, Moisés
author_facet Vidal, Xandro
Mascareñas, José L.
Gulías, Moisés
author_sort Vidal, Xandro
collection PubMed
description [Image: see text] Benzyl and allyltriflamides can engage in Pd-catalyzed oxidative (4+2) annulations with allenes, to produce highly valuable tetrahydroisoquinoline or dihydropyridine skeletons. The reaction is especially efficient when carried out in the presence of designed N-protected amino acids as metal ligands. More importantly, using this type of chiral ligands, it is possible to perform desymmetrizing, annulative C–H activations of prochiral diarylmethylphenyl amides, and thus obtain the corresponding isoquinolines with high enantiomeric ratios.
format Online
Article
Text
id pubmed-6497426
institution National Center for Biotechnology Information
language English
publishDate 2019
publisher American Chemical Society
record_format MEDLINE/PubMed
spelling pubmed-64974262019-05-03 Palladium-Catalyzed, Enantioselective Formal Cycloaddition between Benzyltriflamides and Allenes: Straightforward Access to Enantioenriched Isoquinolines Vidal, Xandro Mascareñas, José L. Gulías, Moisés J Am Chem Soc [Image: see text] Benzyl and allyltriflamides can engage in Pd-catalyzed oxidative (4+2) annulations with allenes, to produce highly valuable tetrahydroisoquinoline or dihydropyridine skeletons. The reaction is especially efficient when carried out in the presence of designed N-protected amino acids as metal ligands. More importantly, using this type of chiral ligands, it is possible to perform desymmetrizing, annulative C–H activations of prochiral diarylmethylphenyl amides, and thus obtain the corresponding isoquinolines with high enantiomeric ratios. American Chemical Society 2019-01-13 2019-02-06 /pmc/articles/PMC6497426/ /pubmed/30636417 http://dx.doi.org/10.1021/jacs.8b12636 Text en Copyright © 2019 American Chemical Society This is an open access article published under a Creative Commons Non-Commercial No Derivative Works (CC-BY-NC-ND) Attribution License (http://pubs.acs.org/page/policy/authorchoice_ccbyncnd_termsofuse.html) , which permits copying and redistribution of the article, and creation of adaptations, all for non-commercial purposes.
spellingShingle Vidal, Xandro
Mascareñas, José L.
Gulías, Moisés
Palladium-Catalyzed, Enantioselective Formal Cycloaddition between Benzyltriflamides and Allenes: Straightforward Access to Enantioenriched Isoquinolines
title Palladium-Catalyzed, Enantioselective Formal Cycloaddition between Benzyltriflamides and Allenes: Straightforward Access to Enantioenriched Isoquinolines
title_full Palladium-Catalyzed, Enantioselective Formal Cycloaddition between Benzyltriflamides and Allenes: Straightforward Access to Enantioenriched Isoquinolines
title_fullStr Palladium-Catalyzed, Enantioselective Formal Cycloaddition between Benzyltriflamides and Allenes: Straightforward Access to Enantioenriched Isoquinolines
title_full_unstemmed Palladium-Catalyzed, Enantioselective Formal Cycloaddition between Benzyltriflamides and Allenes: Straightforward Access to Enantioenriched Isoquinolines
title_short Palladium-Catalyzed, Enantioselective Formal Cycloaddition between Benzyltriflamides and Allenes: Straightforward Access to Enantioenriched Isoquinolines
title_sort palladium-catalyzed, enantioselective formal cycloaddition between benzyltriflamides and allenes: straightforward access to enantioenriched isoquinolines
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6497426/
https://www.ncbi.nlm.nih.gov/pubmed/30636417
http://dx.doi.org/10.1021/jacs.8b12636
work_keys_str_mv AT vidalxandro palladiumcatalyzedenantioselectiveformalcycloadditionbetweenbenzyltriflamidesandallenesstraightforwardaccesstoenantioenrichedisoquinolines
AT mascarenasjosel palladiumcatalyzedenantioselectiveformalcycloadditionbetweenbenzyltriflamidesandallenesstraightforwardaccesstoenantioenrichedisoquinolines
AT guliasmoises palladiumcatalyzedenantioselectiveformalcycloadditionbetweenbenzyltriflamidesandallenesstraightforwardaccesstoenantioenrichedisoquinolines

Ejemplares similares