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Synlett 1994; 1994(7): 521-523
DOI: 10.1055/s-1994-22913
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Organoaluminum-Promoted Direct Conversion of Aldehydes to the Homologous Ketones or Oxiranes with Diazoalkanes

Keiji Maruoka* , Arnel B. Concepcion, Hisashi Yamamoto
  • *School of Engineering, Nagoya University, Chikusa, Nagoya 464-01, Japan
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Publication Date:
18 September 2002 (online)

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Organoaluminum-promoted single homologation of aliphatic and aromatic aldehydes with diazoalkanes has been described. Among various organoaluminum reagents, exceptionally bulky methylaluminum bis(2,6-di-tert-butyl-4-methylphenoxide) (MAD) is found to be highly effective for the selective transformation of aliphatic aldehydes to homologous ketones, while aluminum tris(2,6-diphenylphenoxide) (ATPH) enables the conversion of various aldehydes to oxiranes with diazomethane.