A new synthesis of imidazolidin-2-ones via Pd-catalyzed carboamination of N-allylureas.
A new strategy for the preparation of substituted imidazolidin-2-ones in two steps from readily available N-allylamines is described. Addition of the amine starting materials to isocyanates affords N-allylureas, which are converted to imidazolidin-2-one products with generation of two bonds and up to two stereocenters when treated with aryl bromides and catalytic amounts of Pd2(dba)3/Xantphos in the presence of NaO(t)Bu. [reaction: see text]
Fritz
Jonathan A
JA
Department of Chemistry, University of Michigan, 930 North University Avenue, Ann Arbor, MI 48109-1055, USA.
Nakhla
Josephine S
JS
Wolfe
John P
JP
D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D048289:Imidazolidines / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D014508:Urea / Q000031:analogs & derivatives* / Q000737:chemistry
D048289:Imidazolidines; C095407:2-propenylurea; D010165:Palladium; D014508:Urea