DIASTEREOSELECTIVE α-ALKYLATION OF β-HYDROXY SULFOXIDES AND ITS APPLICATION TO THE SYNTHESIS OF (+)- AND (-)-DISPARLURE

Article abstract of DOI:10.1016/S0040-4039(00)96811-4

α-Alkylation of the dianions of β-hydroxy sulfoxides proceeds with high 1,2-asymmetric induction to give threo-α-alkyl-β-hydroxy sulfoxides.The utility of the present reaction was demonstrated in the asymmetric synthesis of (+)- and (-)-cis-7,8-epoxy-2-methyloctadecanes (disparlure).