JoyaPhos: An Atropisomeric Teraryl Monophosphine Ligand.
C−N cross-coupling
atroposelective synthesis
gold catalysis
monophosphine ligands
palladium catalysis
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
06 Aug 2020
06 Aug 2020
Historique:
received:
13
03
2020
revised:
17
04
2020
pubmed:
20
6
2020
medline:
20
6
2020
entrez:
20
6
2020
Statut:
ppublish
Résumé
A topologically well-defined atropisomeric teraryl monophosphine ligand system, prepared by a highly stereoselective arene-forming aldol condensation combined with a direct ester-to-anthracene transformation, is described herein. The ligands were evaluated for gold(I)-catalyzed [2+2] cycloaddition and cycloisomerization reactions as well as a unique intramolecular Pd-catalyzed C-N cross-coupling for the atroposelective synthesis of a N-aryl-indoline bearing a C-N stereogenic axis. The ligand structure induced up to 95:5 stereoselectivity in the asymmetric allylic alkylation reaction and features an interesting dynamic behavior as observed by X-ray crystallographic studies.
Identifiants
pubmed: 32557961
doi: 10.1002/chem.202001269
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
9864-9868Subventions
Organisme : Schweizerischer Nationalfonds zur Förderung der Wissenschaftlichen Forschung
ID : 155902
Organisme : Schweizerischer Nationalfonds zur Förderung der Wissenschaftlichen Forschung
ID : 175746
Organisme : Schweizerischer Nationalfonds zur Förderung der Wissenschaftlichen Forschung
ID : 182895
Informations de copyright
© 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
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These selectivities further indicate the high enantiomeric purity of the ligands, as based on an expected linear correlation.
Deposition Numbers 1989919 ((Sa)-9), 1989920 ((Sa)-21), 1989921 ((±)-8) and 1989922 ((Sa)-12) contain the supplementary crystallographic data for this paper. These data are provided free of charge by the joint Cambridge Crystallographic Data Centre and Fachinformationszentrum Karlsruhe Access Structures service www.ccdc.cam.ac.uk/structures.