Ouyang Tian-hui
2010
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Journal
Fine chemicals
Abstract
The syntheses of optically active 3-methylthio hexanol and 3-methylthio hexyl actetate were investigated starting from(E)-2-hexenal through reduction,the Sharpless asymmetric epoxidation,regioselective reduction and SN2 nucleophilic substitution.(E)-2-hexenal was reduced by NaBH4 to give(E)-2-hexenol in 91% yield.The optically active 2,3-epoxy hexanol was obtained through the Sharpless asymmetric epoxidation of(E)-2-hexenol with 94% eein 86% yield.2,3-Epoxy hexanol was regioselectively reduced with Red-Al to give optically active 1,3-hexanediol in 82% yield.After the primary hydroxy group of 1,3-hexanediol was transformed to acetate and 3-hydroxy was transformed to mesylate,an SN2 nucleophilic substitution by the reaction with self-made potassium thiomethoxide was carried out to form 3-methylthio hexanol.The overall yield of these three steps was 59%.3-Methylthio hexanol was esterified with acetic anhydride to give 3-methylthio hexyl acetate in 87% yield.The final products of 3-methylthio hexanol and 3-methylthio hexyl actate were obtained with about 94% ee.