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 degrees 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.
Kinder
Robert E
RE
Duke University, French Family Science Center, Durham, North Carolina 27708-0346, USA.
Zhang
Zhibin
Z
Widenhoefer
Ross A
RA
D000466:Alkadienes / Q000737:chemistry*; D001565:Benzoates / Q000138:chemical synthesis*; D002219:Carbamates / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D015394:Molecular Structure; D050607:Organogold Compounds / Q000737:chemistry*; D013237:Stereoisomerism
D000466:Alkadienes; D001565:Benzoates; D002219:Carbamates; D050607:Organogold Compounds; C030011:carbene; C025947:propadiene; D008697:Methane