Oppenauer Oxidation

R. V. Oppenauer, Rec. Trav. Chim. 56, 137 (1937).

The aluminum or potassium alkoxide-catalyzed oxidation of a secondary alcohol to the corresponding ketone (the reverse of the Meerwein-Ponndorf-Verley reduction, q.v.):



T. Beresin in Newer Methods of Preparative Organic Chemistry, English Ed. (Interscience, New York, 1948) p 125; C. Djerassi, Org. React. 6, 207 (1951); L. Horner, U. B. Kaps, Ann. 1980, 192. Intramolecular reactions: B. B. Snider, B. E. man, Tetrahedron 42, 2951 (1986); G. A. Molander, J. A. McKie, J. Am. Chem. Soc. 115, 5821 (1993). Alternate metals: B. Byrne, M. Karras, Tetrahedron Letters 28, 769 (1987); M. L. S. Almeida et al., J. Org. Chem. 61, 6587 (1996); K. Krohn et al., Synthesis 1996, 1341; K. Ishihara et al., J. Org. Chem. 62, 5664 (1997). Review: C. F. de Graauw et al., Synthesis 1994, 1007-1017. Cf. Cannizzaro Reaction.