Control of enantioselectivity in catalytic metal carbene reactions.
Chiral dirhodium(II) complexes constructed from 2-oxopyrrolidine, 2-oxazolidinone, N-acyl-2-imidazolidinone, or 2-azetidinone ligands are exceptional catalysts for enantioselective metal carbene transformations which provide lactones and lactams via cyclopropanation, cyclopropenation, C-H insertion, and ylide reactions with enantiomeric excesses greater than 90% and, usually, in very high yields. These chiral catalysts present high diastereo-, regio- and chemoselectivities, turnover numbers up to 1000, as well as recoverability and reuse.
Doyle
M P
MP
Department of Chemistry, University of Arizona, Tucson 85721-0041, USA. mdoyle@u.arizona.edu
D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods; D006838:Hydrocarbons; D007769:Lactams / Q000737:chemistry; D007783:Lactones / Q000737:chemistry; D008670:Metals; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D008958:Models, Molecular; D008968:Molecular Conformation; D013237:Stereoisomerism
D006838:Hydrocarbons; D007769:Lactams; D007783:Lactones; D008670:Metals; C030011:carbene; D008697:Methane