Palladium-catalyzed aminoallylation of activated olefins with allylic halides and phthalimide

Article abstract of DOI:10.1021/jo025747h

The three-component aminoallylation reaction of the activated olefins 2 with the phthalimide 1a and allyl chloride proceeded very smoothly in the presence of Pd₂dba₃·CHCl₃ (5 mol %)/P(4-FC₆H₄)₃ (40 mol %) and Cs₂CO₃ (3 equiv against 2) in dichloromethane at room temperature to give the corresponding aminoallylated products, N-pent-4-enylphthalimides 3, in 58-99% yields. The reaction of oxazolidinone 1b also proceeded very smoothly to give N-(2,2-dicyano-1-phenylpent-4-enyl)-oxazolidinone in a quantitative yield; however, the Tsuji-Trost-type allylation products 4 were obtained in the case of dibenzylamine, N-tosylaniline, and pyrrolidin-2-one. Further, 2 underwent cycloaddition with N-tosylvinylaziridine 9a in the presence of Pd₂dba₃·CHCl₃ (5 mol %)/P(4-FC₆H₄)₃ (40 mol %) in THF at room temperature, giving the corresponding pyrrolidines 11 in 69-99% yields.