Diastereofacial selectivity in aldol-type condensation induced by optically pure α-sulfinyl acetate with α-substituted aldehydes

Highly diastereoselective aldol-type condensations induced by the chiral magnesium enolate of tert-butyl p-tolyl sulfinyl acetate were performed with optically pure alkyl or hydroxy α-substituted aldehydes. The addition of chiral α-sulfinyl acetate to various aldehydes, α-substituted or not, results mainly with a syn stereochemistry of the two newly created stereocenters. Applications were investigated for the synthesis of syn and trans 1,2-diol models and polysubstituted precursor for natural products.