SYNTHESIS OF BETA-HYDROXY AND GAMMA-HYDROXY SULFONES BY REGIOSELECTIVE OPENING OF BETA,GAMMA-EPOXY SULFONES

β,γ-Epoxy sulfones 1 derived from allylic sulfones react regio-selectively with organomagnesium compounds in the presence or not of catalytic amounts of copper(I) bromide to afford β-hydroxy sulfones 2 or γ-tosylated allylic alcoholates 5 respectively. The Michael type addition of Grignard reagents to intermediates 5 in the presence of catalytic amount of copper(l) bromide yields γ-hydroxy sulfones 6. The PCC oxidation of β- and γ-hydroxy sulfones give β- and γ-oxo sulfones 10 and 11 respectively. In the case of γ-OXO sulfones their treatment with DBU affords α-substituted, α, β- unsaturated carbonyl compounds. © 1990.