Synthesis and use of (E)-1-ethoxy-3-fluoroalkyl-3-hydroxy-4-(4-methylphenylsulfinyl)but-1-enes
Abstract
Condensation of the lithium salt of (R)-methyl p-tolyl sulfoxide 1 with fluorinated α,β-unsaturated ketones 2 leads to (3R/S,RS)-(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
.