A reinvestigation of the Meerwein-Ponndorf-Verley reduction A highly efficient variation using zirconium catalysts

✍ Scribed by Knauer, Birgit ;Krohn, Karsten

• Publisher: John Wiley and Sons
• Year: 1995
• Tongue: English
• Weight: 700 KB
• Volume: 1995
• Category: Article
• ISSN: 0947-3440
• DOI: 10.1002/jlac.199519950496

✦ Synopsis

Reductions I Meerwein-Ponndorf-Verley reaction I Catalysis I Zirconium tetra-tert-butoxide I P-Hydride shift I Kinetics A new variation of the Meenvein-Ponndorf-Verley reduction based on mechanistic considerations is presented. Under optimized conditions 1-(4-dimethylaminophenyl)ethanol was used as the reducing alcohol (2-4 equiv.), Zr(O-tBu)4 as the catalyst (0.2 equiv.), and toluene or cyclohexane as the sol-vent. Aldehydes and ketones (if not extremely sterically hindered) were reduced to the corresponding alcohols at room temperature mostly within 2-4 h in essentially quantitative yield. a,P-Unsaturated carbonyl compounds cleanly react in a 1,2-mode to afford the corresponding allylic alcohols.