Regioselective synthesis of 1, 8-dihydroxytetralins through a tandem reduction/intramolecular hydroxyalkylation of 4-(3-hydroxyphenyl) alkanoates
G Guanti, L Banfi, R Riva
Index: Guanti, Giuseppe; Banfi, Luca; Riva, Renata Tetrahedron, 1994 , vol. 50, # 41 p. 11945 - 11966
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Citation Number: 14
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.
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