SYNTHESIS AND USE OF YL-3-HYDROXY-4-(-4-METHYLPHENYLSULFINYL)BUT-1-ENES

Authors
BRAVO P BRUCHE L FARINA A GERUS II KOLYTCHEVA MT KUKHAR VP MEILLE SV VIANI F
Citation
P. Bravo et al., SYNTHESIS AND USE OF YL-3-HYDROXY-4-(-4-METHYLPHENYLSULFINYL)BUT-1-ENES, Journal of the Chemical Society. Perkin transactions. I, (13), 1995, pp. 1667-1671
Citations number
19
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of the Chemical Society. Perkin transactions. I → ACNP
ISSN journal
0300922X
Issue
13
Year of publication
1995
Pages
1667 - 1671
Database
ISI
SICI code
0300-922X(1995):13<1667:SAUOY>2.0.ZU;2-J
Abstract
Condensation of the lithium salt of (R)-methyl p-tolyl sulfoxide 1 wit h fluorinated alpha,beta-unsaturated ketones 2 leads to kyl-3-hydroxy- 4-(4-methylphenylsulfinyl)but-1-enes 3, whose absolute stereochemistry was determined by X-ray diffraction and NMR analyses. Reductive remov al of the sulfinyl chiral auxiliary allows the preparation of both ena ntiomers of fluorinated tertiary alcohols of type 8 and 9.