Dilithiated 3-tosylpropanal dimethyl acetal as β,β-acylvinyl dianion or homoenolate dianion equivalent

Article abstract of DOI:10.1016/S0040-4020(96)00072-5

3,3-Dilithio-1,1-dimethoxy-3-tosylpropane (6) reacts with mono and dielectrophiles to give dialkylated products 7 and carbocyclic derivatives 8, respectively. Hydrolysis of the acetal function followed by DBU dehydrosulfinylation of these products affords β,β-disubstituted propenal derivatives 11 and 12. Reductive desulfonylation of compounds 8g-j provides β,β-disubstituted propanal acetals 14.