Tetrahedron

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.

~90%

~98%

The growing synthetic utility of the Weinreb amide

[Aidhen, Indrapal Singh; Narasimhan, N. S. Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1993 , vol. 32, # 2 p. 222 - 228]

Tandem reduction/intramolecular hydroxyalkylation of (3-hydr...

[Guanti, Giuseppe; Banfi, Luca; Narisano, Enrica; Riva, Renata; Thea, Sergio Tetrahedron Letters, 1992 , vol. 33, # 27 p. 3919 - 3922]