Diastereoselective Cyclobutenol Synthesis: A Heterogeneous Palladium-Catalyzed Oxidative Carbocyclization-Borylation of Enallenols.
cyclobutenols
diastereoselectivity
enallenols
heterogeneous catalysis
oxidative carbocyclization
palladium
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
02 Jan 2019
02 Jan 2019
Historique:
received:
10
10
2018
pubmed:
12
10
2018
medline:
12
10
2018
entrez:
12
10
2018
Statut:
ppublish
Résumé
A highly selective and efficient oxidative carbocyclization/borylation of enallenols catalyzed by palladium immobilized on amino-functionalized siliceous mesocellular foam (Pd-AmP-MCF) was developed for diastereoselective cyclobutenol synthesis. The heterogeneous palladium catalyst can be recovered and recycled without any observed loss of activity or selectivity. The high diastereoselectivity of the reaction is proposed to originate from a directing effect of the enallenol hydroxyl group. Optically pure cyclobutenol synthesis was achieved by the heterogeneous strategy by using chiral enallenol obtained from kinetic resolution.
Identifiants
pubmed: 30307089
doi: 10.1002/chem.201805118
doi:
Types de publication
Journal Article
Langues
eng
Pagination
210-215Subventions
Organisme : Vetenskapsrådet
ID : 2016-03897
Informations de copyright
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.