Nitroalkanes in Aqueous Medium as an Efficient and Eco-Friendly Source for the One-Pot Synthesis of 1,4-Diketones, 1,4-Diols, δ-Nitroalkanols, and Hydroxytetrahydrofurans
作者:Roberto Ballini、Luciano Barboni、Guido Giarlo
DOI:10.1021/jo0351163
日期:2003.11.1
The Michael addition of primary aliphatic nitro compounds to alpha,beta-unsaturated enones, performed in aqueous media, provides the one-pot synthesis of 1,4-diketones, 1,4-diols, delta-nitroalkanols, and hydroxytetrahydrofurans, respectively, by the appropriate choice of the reaction conditions.
Treatment of secondary nitroalkanes with neat silica-supported 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD), at room temperature, allows the direct conversion of the secondary nitro groups to the corresponding keto carbonyls.