Intermolecular Hydroamination of Allenes with N-Unsubstituted Carbamates Catalyzed by a Gold(I) N-Heterocyclic Carbene Complex

Intermolecular Hydroamination of Allenes with N-Unsubstituted Carbamates Catalyzed by a Gold(I) N-Heterocyclic Carbene Complex

Reaction of 2,3-pentadienyl benzoate with benzyl carbamate catalyzed by a 1:1 mixture of (NHC)AuCl and AgOTf in dioxane at 23 °C for 5 h led to isolation of (E)-4-(benzyloxycarbonylamino)-2-pentenyl benzoate in 84% yield as a single regio- and diastereomer. Gold(I)-catalyzed hydroamination was effec...

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Veröffentlicht in:Organic letters 2008-07, Vol.10 (14), p.3157-3159
Hauptverfasser: Kinder, Robert E, Zhang, Zhibin, Widenhoefer, Ross A
Format: Artikel
Sprache:eng
Schlagworte:
Alkadienes - chemistry
Benzoates - chemical synthesis
Carbamates - chemistry
Catalysis
Combinatorial Chemistry Techniques
Methane - analogs & derivatives
Methane - chemistry
Molecular Structure
Organogold Compounds - chemistry
Stereoisomerism
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Zusammenfassung:Reaction of 2,3-pentadienyl benzoate with benzyl carbamate catalyzed by a 1:1 mixture of (NHC)AuCl and AgOTf in dioxane at 23 °C for 5 h led to isolation of (E)-4-(benzyloxycarbonylamino)-2-pentenyl benzoate in 84% yield as a single regio- and diastereomer. Gold(I)-catalyzed hydroamination was effective for a number of N-unsubstituted carbamates and a range of substituted allenes.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol8010858