Meerwein-Ponndorf-Verley reduction

Meerwein-Ponndorf-Verley reduction

The Meerwein-Ponndorf-Verley Reduction in organic chemistry is the reduction of ketones to secondary alcohols with aluminumisopropylate catalysis in isopropanol solution [Alexander R. Surrey, Name Reactions in Organic Chemistry, 2nd Edition, Academic Press, 1961.] [Kurti and Czako, Strategic Application of Named Reaction in Organic Synthesis, Elsevier Academic Press, 2005.] .


Reduction of a ketone 1 to the alcohol 3 in the presence of aluminumisopropylate 2.

First the carbonyl-oxygen coordinates to the aluminumisopropylate 2. This makes the carbonyl-carbon even more positive. In the next step the hydride attacks the carbonyl-carbon and a 6-membered cyclic transition state is formed. After the hydride shift the alcoholate of the desired alcohol 5 and acetone 6 remain. The alcoholate reacts with another isopropanol molecule to form the alcohol 3 and recover the Aluminumisopropylate.

All of these reactions are reversible, and complete conversion can be achieved by employing excess alcohol as the reaction solvent or by removal of acetone from the reaction mixture by distillation.

The same process in the opposite direction is called Oppenauer oxidation.

References

*cite journal
title = Ein neues Verfahren zur Reduktion von Aldehyden und Ketonen
author = Hans Meerwein, Rudolf Schmidt
journal = Justus Liebigs Annalen der Chemie
volume = 444
issue = 1
pages = 221 - 238
year = 1924
url =
doi = 10.1002/jlac.19254440112

*cite journal
title = Der reversible Austausch der Oxydationsstufen zwischen Aldehyden oder Ketonen einerseits und primären oder sekundären Alkoholen anderseits
author = Wolfgang Ponndorf
journal = Angewandte Chemie
volume = 39
issue = 5
pages = 138-143
year = 1926
url =
doi = 10.1002/ange.19260390504

*cite journal
title =
author = Verley, A.,
journal = Bull. Soc. Chim. Fr.
volume = 37
issue =
pages = 537
year = 1925
url =
doi =

*cite journal
title = Mechanism of the Meerwein–Ponndorf Reduction
author = L. M. Jackman; J. A. Mills
journal = Nature
volume = 164
issue =
pages = 789-790
year = 1949
url =
doi = 10.1038/164789a0


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