Meerwein-Ponndorf-Verley Reduction

The aluminium-catalyzed hydride shift from the a-carbon of an alcohol component to the carbonyl carbon of a second component, which proceeds via a six-membered transition state, is referred to as the Meerwein-Ponndorf-Verley Reduction (MPV) or the Oppenauer Oxidation, depending on which component is the desired product. If the alcohol is the desired product, the reaction is viewed as the Meerwein-Ponndorf-Verley Reduction.

Isopropanol is useful as a hydride donor because the resulting acetone may be continuously removed from the reaction mixture by distillation.

Grignard Reagents will sometimes yield the result of an MPV reduction if the carbonyl carbon is too hindered for nucleophilic addition.

Recent Literature

Transfer Hydrogenation of Carbonyl Derivatives Catalyzed by an Inexpensive Phosphine-Free Manganese Precatalyst
A. Bruneau-Voisine, D. Wang, V. Dorcet, T. Roisnel, C. Darcel, J.-B. Sortais, Org. Lett., 2017, 19, 3656-3659.

Catalytic Meerwein-Pondorf-Verley Reduction by Simple Aluminum Complexes
E. J. Campbell, H. Zhou, S. T. Nguyen, Org. Lett., 2001, 3, 2391-2393.

Indium Tri(isopropoxide)-Catalyzed Selective Meerwein-Ponndorf-Verley Reduction of Aliphatic and Aromatic Aldehydes
J. Lee, T. Ryu, S. Park, P. H. Lee, J. Org. Chem., 2012, 77, 4821-4825.

Lithium Bromide as a Flexible, Mild, and Recyclable Reagent for Solvent-Free Cannizzaro, Tishchenko, and Meerwein-Ponndorf-Verley Reactions
M. M. Mojtahedi, E. Akbarzadeh, R. Sharifi, M. S. Abaee, Org. Lett., 2007, 9, 2791-2793.

Hydrogen-Transfer Catalysis with Pincer-Aryl Ruthenium (II) Complexes
P. Dani, T. Karlen, R. A. Gossage, S. Gladiali, G. van Koten, Angew. Chem. Int. Ed., 2000, 39, 743-745.

Catalytic Meerwein-Ponndorf-Verley (MPV) and Oppenauer (OPP) Reactions: Remarkable Acceleration of the Hydride Transfer by Powerful Bidentate Aluminum Alkoxides
T. Ooi, T. Miura, Y. Itagaki, H. Ichikawa, K. Maruoka, Synthesis, 2002, 279-291

Highly Diastereoselective Catalytic Meerwein-Ponndorf-Verley Reductions
J. Yin, M. A. Huffman, K. M. Conrad, J. D. Armstrong, J. Org. Chem., 2006, 71, 840-843.

Highly Diastereoselective Catalytic Meerwein-Ponndorf-Verley Reductions
J. Yin, M. A. Huffman, K. M. Conrad, J. D. Armstrong, J. Org. Chem., 2006, 71, 840-843.

Reduction of Carbonyl Compounds by Lanthanide Metal/2-Propanol: In-situ Generation of Samarium Isopropyloxide for Stereoselective Meerwein-Ponndorf-Verley Reduction
S.-I. Fukuzawa, N. Nakano, T. Saitoh, Eur. J. Org. Chem., 2004, 2863-2867.

A Mild and Efficient Flow Procedure for the Transfer Hydrogenation of Ketones and Aldehydes using Hydrous Zirconia
C. Battilocchio, J. M. Hawkins, S. V. Ley, Org. Lett., 2013, 15, 2278-2281.