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

Andrew J. Wommack, David C. Moebius, Austin L. Travis and Jason S. Kingsbury*

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

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

DOI: 10.1021/ol9010932 (free Supporting Information)


Abstract

A mild procedure enables a convergent ketone assembly from nonstabilized diazoalkanes and aldehydes, including examples of chiral ketone synthesis with disubstituted (internal) nucleophiles. The method’s remarkable tolerance to steric crowding is showcased in a simple approach to achyrofuran, a complex dibenzofuran.

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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

Ketones, Diazo Compounds


ID: J54-Y2009-2290