β,γ-EPOXY SULFONES IN ORGANIC SYNTHESIS. PART 2: PREPARATION OF β,γ-BIFUNCIONALIZED SULFONES

Article abstract of DOI:10.1016/S0040-4020(01)87131-3

Heteronucleophiles reagents react with β,γ-epoxy sulfones 1 at the γ position in the presence of Ti(OPrⁱ)4 or magnesium halides to afford regioselectively γ-functionalized β-hydroxy sulfones 2.With soft nucleophiles such as sodium azide, triphenylphosphine, or sodium benzethiolate the reaction takes place in the absence of Lewis acids.In the case of basic reagents such as sodium methoxide or diethylamine the corresponding regioisomers, the β-functionalized γ-hydroxy sulfones 3 were exclusively obtained.The preparation of compounds 3 (R² = H) was also carried out starting from 3-tosyl-2-propen-1-ol (4) by Michael addition of different heteronucleophiles.