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Gold(I)-catalyzed intramolecular dihydroamination of allenes with N,N'-disubstituted ureas to form bicyclic imidazolidin-2-ones.
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ABSTRACT:
SUBMITTER: Li H
PROVIDER: S-EPMC2813268 | biostudies-other | 2009 Jun
REPOSITORIES: biostudies-other
Publications
Gold(I)-catalyzed intramolecular dihydroamination of allenes with N,N'-disubstituted ureas to form bicyclic imidazolidin-2-ones.
Organic letters 20090601 12
Reaction of N-delta-allenyl urea 1 with a catalytic 1:1 mixture of gold(I) N-heterocyclic carbene complex (5)AuCl [5 = 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidine] and AgPF(6) at room temperature for 2 h led to isolation of bicyclic imidazolidin-2-one 4 in 93% yield with >or=98% diastereomeric purity. Gold-catalyzed dihydroamination was effective for a number of N-delta- and N-gamma-allenyl ureas to form the corresponding bicyclic imidazolidin-2-ones in good yield with high diastereoselecti ...[more]