Palladium-catalyzed ring-forming aminoacetoxylation of alkenes.
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
Erik J
EJ
Department of Chemistry, Princeton University, Princeton, New Jersey 08544, USA.
Lee
Chulbom
C
Sorensen
Erik J
EJ
D000107:Acetylation; D000475:Alkenes / Q000737:chemistry*; D000586:Amination; D002384:Catalysis; D003500:Cyclization; D006571:Heterocyclic Compounds / Q000138:chemical synthesis*; D010084:Oxidation-Reduction; D010165:Palladium / Q000737:chemistry
D000475:Alkenes; D006571:Heterocyclic Compounds; D010165:Palladium