Regioselective synthesis of 1,8-dihydroxytetralins through a tandem reduction/intramolecular hydroxyalkylation of 4-(3-hydroxyphenyl)alkanoates

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Abstract

A series of 4-(3-hydroxyphenyl)butanoates 3 has been prepared and transformed into 1,8-dihydroxytetralins of general formula 2 by treatment with 2 equivalents of DIBALH followed by quenching with aqueous NH4Cl. A possible mechanism for this novel totally regioselective intramolecular hydroxyalkylation is suggested and the factors affecting the stability of 1,8-dihydroxytetralins 2 are also discussed. © 1994.

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Guanti, G., Banfi, L., & Riva, R. (1994). Regioselective synthesis of 1,8-dihydroxytetralins through a tandem reduction/intramolecular hydroxyalkylation of 4-(3-hydroxyphenyl)alkanoates. Tetrahedron, 50(41), 11945–11966. https://doi.org/10.1016/S0040-4020(01)89307-8

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