Cross-metathesis reactions of 1-hepten-3-ol, 1-octen-4-ol, 1-octen-4-yl acetate and 1-tetradecen-4-ol with unsaturated methyl esters were investigated to optimize the synthesis of methyl hydroxyalkenoates, precursors of hydroxyalkanoic acids. Various commercially available catalysts, concentration ratios of reagents as well as microwave irradiation were explored. (R)-8-hydroxydodecanoic acid and (S)-8-hydroxystearic acid were successfully obtained in 3 steps from enantiomerically enriched alcohols.
An Efficient Synthesis of Chiral Non‐Racemic Hydroxyalkanoic Acids by Olefin Cross‐Metathesis Reactions
Asaro, Fioretta;Drioli, Sara;Forzato, Cristina;Nitti, Patrizia
2018-01-01
Abstract
Cross-metathesis reactions of 1-hepten-3-ol, 1-octen-4-ol, 1-octen-4-yl acetate and 1-tetradecen-4-ol with unsaturated methyl esters were investigated to optimize the synthesis of methyl hydroxyalkenoates, precursors of hydroxyalkanoic acids. Various commercially available catalysts, concentration ratios of reagents as well as microwave irradiation were explored. (R)-8-hydroxydodecanoic acid and (S)-8-hydroxystearic acid were successfully obtained in 3 steps from enantiomerically enriched alcohols.File in questo prodotto:
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