Highly selective catalyst-directed pathways to dihydropyrroles from vinyldiazoacetates and imines.
Copper-catalyzed reactions of vinyldiazoacetates with imines occur via a pathway in which the activated imine undergoes electrophilic addition to the vinyldiazo compound, whereas reactions catalyzed by rhodium(II) proceed through a metal carbene to an intermediate iminiumylide. Both pathways exhibit high stereoselectivities.
Doyle
Michael P
MP
Department of Chemistry, University of Arizona, Tucson, Arizona 85721-0041, USA. mdoyle@u.arizona.edu
Yan
Ming
M
Hu
Wenhao
W
Gronenberg
Luisa S
LS
D000085:Acetates / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry; D007097:Imines / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D012238:Rhodium / Q000737:chemistry; D014753:Vinyl Compounds / Q000737:chemistry*
D000085:Acetates; D007097:Imines; D011758:Pyrroles; D014753:Vinyl Compounds; C013231:pyrroline; D003300:Copper; D012238:Rhodium