Journal
CHEMICAL & PHARMACEUTICAL BULLETIN
Volume 52, Issue 2, Pages 287-288Publisher
PHARMACEUTICAL SOC JAPAN
DOI: 10.1248/cpb.52.287
Keywords
carbonyl compound; niobium; pinacol coupling; vicinal diol; zinc
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A simple method for the diastereoselective synthesis of racemic 1,2-diol mediated by low-valence niobium generated in situ is described. A 1,4-dioxane-toluene solvent system was found to be essential to achieve higher selectivities and to prevent other reactions of pinacols, such as deoxygenation and acetal formation. Aromatic aldehydes and ketones were converted to the corresponding pinacols with up to 97 and 85% de, respectively.
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