Practical Oppenauer (OPP) Oxidation of Alcohols with a Modified Aluminum Catalyst

Takashi Ooi, Hidehito Otsuka, Tomoya Miura, Hayato Ichikawa, and Keiji Maruoka*
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 6068502
Org. Lett., 2002, 4 (16), pp 2669–2672
DOI: 10.1021/ol020094c
Publication Date (Web): July 9, 2002
Copyright © 2002 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, maruoka@kuchem.kyoto-u.ac.jp

Abstract

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Modified aluminum catalyst 2 was found to be highly effective for Oppenauer (OPP) oxidation of alcohols under mild conditions. For example, oxidation of carveol in toluene with t-BuCHO (1.2 equiv) as a hydride acceptor in the presence of 2 (1 mol %) proceeded smoothly at 21 °C to give carvone in 94% yield after 1 h. A practical aspect of this system was highlighted by the facile OPP oxidation of terpenoids and steroids with 1.2−3.0 equiv of acetone and 2 (3−5 mol %).

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History

  • Published In Issue August 08, 2002
  • Received May 6, 2002

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