Enantioselective Carbocycle Formation through Intramolecular Pd-Catalyzed Allyl–Aryl Cross-Coupling

Enantioselective Carbocycle Formation through Intramolecular Pd-Catalyzed Allyl–Aryl Cross-Coupling

Aryl electrophiles containing tethered allylboronate units undergo efficient intramolecular coupling in the presence of a chiral palladium catalyst to give enantioenriched carbocyclic products. The reaction is found to be quite general, affording 5, 6, and 7-membered carbocyclic products as single r...

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Veröffentlicht in:Organic letters 2014-09, Vol.16 (17), p.4420-4423
Hauptverfasser: Schuster, Christopher H, Coombs, John R, Kasun, Zachary A, Morken, James P
Format: Artikel
Sprache:eng
Schlagworte:
Boronic Acids - chemistry
Catalysis
catalysts
catalytic activity
cross-coupling reactions
Cyclization
enantioselectivity
Letter
Lewis acids
Molecular Structure
organic compounds
palladium
Palladium - chemistry
Polycyclic Compounds - chemical synthesis
Polycyclic Compounds - chemistry
positional isomers
Stereoisomerism
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Beschreibung
Zusammenfassung:Aryl electrophiles containing tethered allylboronate units undergo efficient intramolecular coupling in the presence of a chiral palladium catalyst to give enantioenriched carbocyclic products. The reaction is found to be quite general, affording 5, 6, and 7-membered carbocyclic products as single regioisomers and with moderate enantioselectivities. Examination of differential coupling partners points to rapid allyl-equilibration as a key stereodefining feature.
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/ol5019163