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Highly Efficient and Enantioselective α-Arylation of Cycloalkanones by Scandium-Catalyzed Diazoalkane-Carbonyl Homologation

Victor L. Rendina, Hilan Z. Kaplan, Jason S. Kingsbury*

*Eugene F. Merkert Chemistry Center, Boston College, 2609 Beacon St., Chestnut Hill, MA 02467, USA, Email:

V. L. Rendina, H. Z. Kaplan, J. S. Kingsbury, Synthesis, 2012, 44, 686-693.

DOI: 10.1055/s-0031-1289650


Functionalized α-tertiary and -quaternary 2-arylcycloalkanones are rapidly accessed by scandium(III) triflate-catalyzed diazoalkane-carbonyl homologations. Pairing readily available bis- and tris(oxazoline) based ligands with scandium triflate allows access to arylated medium ring carbocycles with high enantioselectivities and excellent yields.

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Catalytic and Regioselective Ring Expansion of Arylcyclobutanones with Trimethylsilyldiazomethane. Ligand-Dependent Entry to β-Ketosilane or Enolsilane Adducts

J. A. Dabrowski, D. C. Moebius, A. J. Wommack, A. F. Kornahrens, J. S. Kingsbury, Org. Lett., 2010, 12, 3598-3601.

Key Words

diazo compounds, scandium, asymmetric catalysis, ring expansion, arylation, cyclopentanones, cycloheptanones

ID: J66-Y2012-0520