Tetrahedron p. 11945 - 11966 (1994)
Update date:2022-08-05
Topics: Regioselective synthesis
Guanti, Giuseppe
Banfi, Luca
Riva, Renata
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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