ON THE DIHYDROXYLATION OF CYCLIC ALLYLIC ALCOHOLS

Authors
DONOHOE TJ GARG R MOORE PR
Citation
Tj. Donohoe et al., ON THE DIHYDROXYLATION OF CYCLIC ALLYLIC ALCOHOLS, Tetrahedron letters, 37(19), 1996, pp. 3407-3410
Citations number
20
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
37
Issue
19
Year of publication
1996
Pages
3407 - 3410
Database
ISI
SICI code
0040-4039(1996)37:19<3407:OTDOCA>2.0.ZU;2-5
Abstract
The preparation and dihydroxylation (OsO4) of a series of conformation ally constrained allylic alcohols is described. By using dichlorometha ne as solvent, the selectivity that favours the anti triol is substant ially reduced by hydrogen-bonding effects. This principle is applied t o the stereoselective synthesis of syn tetraols from the oxidation of (1S,2S)-1,2-dihydroxy-3-bromo-3,5-cyclohexadiene. (C) 1996 Elsevier Sc ience Ltd