Journal
ORGANIC LETTERS
Volume 11, Issue 12, Pages 2671-2674Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol900730w
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Funding
- NIH [GM-080422]
- Johnson Johnson
- NCBC [2008-IDG-1010]
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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 AgPF6 at room temperature for 2 h led to isolation of bicyclic imidazolidin-2-one 4 in 93% yield with >= 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 diastereoselectivity.
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