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

Jennifer A. Dabrowski, David C. Moebius, Andrew J. Wommack, Anne F. Kornahrens and Jason S. Kingsbury*

*Department of Chemistry, Eugene F. Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, Email: jason.kingsburypomona.edu

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

DOI: 10.1021/ol101136a

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Abstract

The homologation of arylcyclobutanones with trimethylsilyldiazomethane gives enolsilanes in the presence of Sc(OTf)₃ as catalyst with a high preference for methylene migration, whereas Sc(hfac)₃ leads to β-ketosilanes. Each adduct affords the cyclopentanone upon hydrolysis.

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

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

Diverse Alkanones by Catalytic Carbon Insertion into the Formyl C-H Bond. Concise Access to the Natural Precursor of Achyrofuran

A. J. Wommack, D. C. Moebius, A. L. Travis, J. S. Kingsbury, Org. Lett., 2009, 11, 3202-3205.

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Key Words

Cyclopentanones, Ring Expansions

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ID: J54-Y2010-2220