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A mild, palladium(II)-catalyzed ring-forming aminoacetoxylation of alkenes is described. Treatment of a range of nitrogen nucleophiles with catalytic palladium(II) in the presence of PhI(OAc)2 as oxidant resulted in alkene aminoacetoxylation, affording a variety of nitrogen-containing heterocycles. Our studies indicate the possibility for high levels of reaction regio- and stereocontrol. It appears that this is a stereoselective trans alkene difunctionalization and thus a useful alternative to related cis-selective, metal-catalyzed alkene aminohydroxylation processes.
Alexanian et al. (2005) studied this question.