Luche Reduction

The Selective 1,2-reduction Of Enones With Sodium Borohydride Is Achieved In Combination With CeCl₃.

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Mechanism Of The Luche Reduction

CeCl₃ is A Selective Lewis Acid Catalyst For The Methanolysis Of Sodium Borohydride. The Resulting Reagents, Various Sodium Methoxyborohydrides, Are Harder Reducing Agents (according To HSAB Principles) And Therefore Effect An 1,2-reduction With Higher Selectivity.

Furthermore, CeCl₃ activates Methanol.

Recent Literature

Reduction Of Ketones To Alcohols Using A Decaborane/pyrrolidine/cerium(III) Chloride System In Methanol
J. W. Bae, S. H. Lee, Y. J. Jung, C.-O. M. Yoon, C. M. Yoon, Tetrahedron Lett., 2001, 42, 2137-2139.

Asymmetric 1,2-Reduction Of Enones With Potassium Borohydride Catalyzed By Chiral N,N'-Dioxide-Scandium(III) Complexes
P. He, X. Liu, H. Zheng, W. Li, L. Lin, X. Feng, Org. Lett., 2012, 14, 5134-5137.

Recent Literature

Reduction Of Ketones To Alcohols Using A Decaborane/pyrrolidine/cerium(III) Chloride System In Methanol
J. W. Bae, S. H. Lee, Y. J. Jung, C.-O. M. Yoon, C. M. Yoon, Tetrahedron Lett., 2001, 42, 2137-2139.

Asymmetric 1,2-Reduction Of Enones With Potassium Borohydride Catalyzed By Chiral N,N'-Dioxide-Scandium(III) Complexes
P. He, X. Liu, H. Zheng, W. Li, L. Lin, X. Feng, Org. Lett., 2012, 14, 5134-5137.

Chemoselective Luche-Type Reduction Of α,β-Unsaturated Ketones By Magnesium Catalysis
Y. K. Jang, M. Magre, M. Rueping, Org. Lett., 2019, 21, 8349-8352.

Applications Of Lanthanide Trichloride Hydrates Prepared From Mischmetall In Luche-Type Reduction
M.-I. Lannou, F. Hélion, J.-L. Namy, Synlett, 2007, 2707-2710.

A Facile Approach To The Synthesis Of Allylic Spiro Ethers And Lactones
M.-C. P. Yeh, Y.-C. Lee, T.-C. Young, Synthesis, 2006, 3621-3624.

Chemoselective Luche-Type Reduction Of α,β-Unsaturated Ketones By Magnesium Catalysis
Y. K. Jang, M. Magre, M. Rueping, Org. Lett., 2019, 21, 8349-8352.

Applications Of Lanthanide Trichloride Hydrates Prepared From Mischmetall In Luche-Type Reduction
M.-I. Lannou, F. Hélion, J.-L. Namy, Synlett, 2007, 2707-2710.

A Facile Approach To The Synthesis Of Allylic Spiro Ethers And Lactones
M.-C. P. Yeh, Y.-C. Lee, T.-C. Young, Synthesis, 2006, 3621-3624.