Allenes as Carbon Nucleophiles in Palladium-Catalyzed Reactions:  Observation of Anti Attack of Allenes on (π-Allyl)palladium Complexes

Allenes as Carbon Nucleophiles in Palladium-Catalyzed Reactions:  Observation of Anti Attack of Allenes on (π-Allyl)palladium Complexes

In the palladium-catalyzed cyclization of allenic allylic esters using Pd(dba)2 as catalyst, it was shown that the allene acts as a carbon nucleophile. Intermediates were isolated and stereochemical studies established that the double bond of the allene has attacked the (π-allyl)palladium intermedia...

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Veröffentlicht in:Journal of the American Chemical Society 2002-09, Vol.124 (38), p.11246-11247
Hauptverfasser: Franzén, Johan, Löfstedt, Joakim, Dorange, Ismet, Bäckvall, Jan-E
Format: Artikel
Sprache:eng
Schlagworte:
4-ADDITION
4-OXIDATION
ALLYLIC ALKYLATION
ALLYLSILANES
BOND FORMATION
CARBOPALLADATION
Chemical reactivity
Chemistry
CONJUGATED DIENES
CYCLIZATION
Exact sciences and technology
ISOMERIZATION
Kemi
LIGANDS
NATURAL SCIENCES
NATURVETENSKAP
Organic chemistry
Reactivity and mechanisms
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Zusammenfassung:In the palladium-catalyzed cyclization of allenic allylic esters using Pd(dba)2 as catalyst, it was shown that the allene acts as a carbon nucleophile. Intermediates were isolated and stereochemical studies established that the double bond of the allene has attacked the (π-allyl)palladium intermediate on the face opposite to that of palladium.
ISSN:0002-7863
1520-5126
1520-5126
DOI:10.1021/ja026150m