(E)-4-LITHIO-4-TOSYLBUTENONE DIMETHYL KETAL: A NEW β-ACYLVINYL ANION EQUIVALENT

Article abstract of DOI:10.1016/S0040-4039(00)96952-1

(E)-4-Lithio-4-tosylbutenone dimethyl ketal is regio and stereoselectively prepared by direct lithiation of the corresponding precursor with methyl-lithium at -20 deg C; the reaction of this β-acylvinyl anion equivalent with different electrophilic reagents (H2O, D2O, Me3SiCl, Me2S2, MeI, CH2=CHCH2Br, BuⁱCHO, PhCHO, PhCOCl, Ac2O) affords the corresponding functionalized compounds.