A rhodium IBiox[(-)-menthyl] complex as a highly selective catalyst for the asymmetric hydroarylation of azabicyles: an alternative route to epibatidine.
The synthesis and characterization of a new chiral rhodium N-heterocyclic carbene complex, Rh(IBiox[(-)-menthyl](CO)(2)Cl, is reported. In addition, the very high enantioselectivity exhibited by this complex, as a catalyst for the asymmetric hydroarylation of azabicycles, is demonstrated and applied to the synthesis of epibatidine.
Bexrud
Jason
J
Department of Chemistry, University of Toronto, Toronto, Ontario, Canada M5S 3H6.
Lautens
Mark
M
D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000737:chemistry*; D002384:Catalysis; D009942:Organometallic Compounds / Q000737:chemistry*; D011725:Pyridines / Q000737:chemistry*; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
D019086:Bridged Bicyclo Compounds, Heterocyclic; D009942:Organometallic Compounds; D011725:Pyridines; D012238:Rhodium; C082748:epibatidine