SYNTHESIS AND USE OF (E)-1-ETHOXY-3-FLUOROALKYL-3-HYDROXY-4-(-4-METHYLPHENYLSULFINYL)BUT-1-ENES

Condensation of the lithium salt of (R)-methyl p-tolyl sulfoxide 1 with fluorinated alpha,beta-unsaturated ketones 2 leads to (3R/S,R(s),)-(E)-1-ethoxy-3-fluoroalkyl-3-hydroxy-4-(4-methylphenylsulfinyl)but-1-enes 3, whose absolute stereochemistry was determined by X-ray diffraction and NMR analyses. Reductive removal of the sulfinyl chiral auxiliary allows the preparation of both enantiomers of fluorinated tertiary alcohols of type 8 and 9.