3-Benzyloxy-1-isocyanopropenes. Synthesis and use as 3-hydroxypropanoyl anion equivalents

Article abstract of DOI:10.1016/0040-4039(96)00312-7

New acyl anion equivalents bearing a hydroxyl group at the β-position have been developed. Treatment of 3-benzyloxy-1-isocyanopropenes with lithium diisopropylamide (LDA) in THF at -78°C generated the 1-lithio compounds, which reacted with alkyl halides to afford the corresponding 1-alkylated products in good yields. Acid hydrolysis of these alkylated products followed by hydrogenolysis of the resulting β-benzyloxyethyl ketones led to β-hydroxyethyl ketones.