10.1246/cl.2012.325
The research focuses on the isomerization of glycidic esters to β-hydroxy-α,ω-unsaturated esters (allylic alcohols) using HClO4·SiO2 as an efficient catalyst. This method was applied in the formal synthesis of (R)-Baclofen and α-phenyl GABA analogues. The study found that HClO4·SiO2 is a stable and effective reagent for this transformation, yielding allylic alcohols in good to high yields. These allylic alcohols were then converted into GABA derivatives through selective SN2 nucleophilic substitution with azide ion, followed by hydrogenation and reduction steps. The key chemicals involved in this research include glycidic esters derived from various ketones, HClO4·SiO2 as the catalyst, azide ion for the nucleophilic substitution, and palladium on carbon (Pd/C) for hydrogenation. The study also utilized methanesulfonyl chloride (MsCl) and sodium azide (NaN3) in the conversion process. The results demonstrate a new and efficient route for synthesizing important GABA derivatives, such as Baclofen, using readily available reagents and mild reaction conditions.