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 4-(3-Hydroxyphenyl)-alkanoates: a New Regioselective Approach to 1,8-Dihydroxytetralins
GUANTI, GIUSEPPE;BANFI, LUCA;RIVA, RENATA;THEA, SERGIO
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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