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A reinvestigation of the Meerwein‐Ponndorf‐Verley reduction A highly efficient variation using zirconium catalysts
Author(s) -
Knauer Birgit,
Krohn Karsten
Publication year - 1995
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.199519950496
Subject(s) - chemistry , cyclohexane , allylic rearrangement , toluene , catalysis , yield (engineering) , alcohol , zirconium , steric effects , ethanol , solvent , organic chemistry , medicinal chemistry , materials science , metallurgy
A new variation of the Meerwein‐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‐ t Bu) 4 as the catalyst (0.2 equiv.), and toluene or cyclohexane as the solvent. 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. α,β‐Unsaturated carbonyl compounds cleanly react in a 1,2‐mode to afford the corresponding allylic alcohols.