CYCLIC CHIRAL DIOLS WITH C-2 SYMMETRY - SYNTHESIS OF (2R,3R)-DIHYDROXY-1,2,3,4-TETRAHYDRONAPHTHALENE

Authors
ORSINI F PELIZZONI F
Citation
F. Orsini et F. Pelizzoni, CYCLIC CHIRAL DIOLS WITH C-2 SYMMETRY - SYNTHESIS OF (2R,3R)-DIHYDROXY-1,2,3,4-TETRAHYDRONAPHTHALENE, Tetrahedron : asymmetry, 7(4), 1996, pp. 1033-1040
Citations number
17
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
7
Issue
4
Year of publication
1996
Pages
1033 - 1040
Database
ISI
SICI code
0957-4166(1996)7:4<1033:CCDWCS>2.0.ZU;2-M
Abstract
(2R, 3R)-dihydroxy-tetrahydronaphthalene 4 has been prepared via an ef ficient three-step synthesis from cis-(1R, 2S)-dihydroxy-1,2-dihydrona phthalene 1. The latter was obtained by bioconversion of naphthalene b y a modified strain of Pseudomonas fluorescens. The diol 4 has been su ccessfully tested in a conjugate asymmetric addition of lithium dibuty l cuprate to the monocrotonate 7. Copyright (C) 1996 Elsevier Science Ltd