4-(3-hydroxyphenyl)-butanoates 4, on treatment with DIBALH, followed by hydrolytic work-up, undergo a novel completely regioselective intramolecular hydroxyalkylation reaction to give 1,8-dihydroxytetralins. The yield of the reaction depends heavily on the structure of starting material, best results being achieved with 3,3-disubstituted butanoates.
TANDEM REDUCTION INTRAMOLECULAR HYDROXYALKYLATION OF (3-HYDROXYPHENYL)ALKANOATES - A NEW REGIOSELECTIVE APPROACH TO 1,8-DIHYDROXYTETRALINS
GUANTI, G;NARISANO, E;RIVA, R;THEA, S
1992-01-01
Abstract
4-(3-hydroxyphenyl)-butanoates 4, on treatment with DIBALH, followed by hydrolytic work-up, undergo a novel completely regioselective intramolecular hydroxyalkylation reaction to give 1,8-dihydroxytetralins. The yield of the reaction depends heavily on the structure of starting material, best results being achieved with 3,3-disubstituted butanoates.
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