Meerwein-Ponndorf-Verley Reduction (Aluminum Alkoxide Reduction)

H. Meerwein, R. Schmidt, Ann. 444, 221 (1925); W. Ponndorf, Angew. Chem. 39, 138 (1926); A. Verley, Bull. Soc. Chim. France 37, 537, 871 (1925).

Reduction of aldehydes or ketones to the corresponding alcohols with aluminum alkoxides (the reverse of the Oppenauer oxidation, q.v.):

Reviews: A. L. Wilds, Org. React. 2, 178-202 (1944); R. M. Kellogg, Comp. Org. Syn. 8, 88-91 (1991); C. F. de Graauw et al., Synthesis 10, 1007-1017 (1994). Enantioselectivity: D. A. Evans et al., J. Am. Chem. Soc. 115, 9800 (1993); M. Node et al., ibid. 122, 1927 (2000). Modified conditions: P. S. Kumbhar et al., Chem. Commun., 1998, 535; T. Ooi et al., J. Am. Chem. Soc. 120, 10790 (1998); Y. Nakano et al., Tetrahedron Letters 41, 1565 (2000). Cf. Cannizzaro Reaction; Tischenko Reaction.