Amplification of asymmetric induction in sequential reactions of bis-diazoacetates catalyzed by chiral dirhodium(II) carboxamidates.
[reaction: see text] Two sequential intramolecular carbon-hydrogen insertion or cyclopropanation reactions of bis-diazoacetates using chiral dirhodium(II) carboxamidate catalysts are reported. The initial metal carbene transformation forms an excess of one enantiomer that with the second transformation further enhances stereocontrol (kinetic amplification). Diastereoselectivity and enantioselectivity for product formation are controlled by the catalyst.
Doyle
Michael P
MP
Department of Chemistry and Biochemistry, University of Maryland, College Park, 20742, USA. mdoyle3@umd.edu
Wang
Yuanhua
Y
Ghorbani
Pejman
P
Bappert
Erhard
E
D000085:Acetates / Q000737:chemistry*; D002384:Catalysis; D003979:Diazonium Compounds / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism
D000085:Acetates; D003979:Diazonium Compounds; D006571:Heterocyclic Compounds; D009942:Organometallic Compounds; D012238:Rhodium