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

DOI: 10.1016/S0040-4020(01)89307-8

Source and publish data:

Tetrahedron p. 11945 - 11966 (1994)

Update date:2022-08-05

Topics: Regioselective synthesis

Authors:

Guanti, Giuseppe

Banfi, Luca

Riva, Renata

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Article abstract of DOI:10.1016/S0040-4020(01)89307-8

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.

Full text of DOI:10.1016/S0040-4020(01)89307-8

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