Synthesis of enantiomerically pure β-hydroxy-γ-sulfinylaldehyde dimethyl acetals

Article abstract of DOI:10.1016/0957-4166(96)00217-0

Lithium alkyl p-tolylsulfinyl anions generated from 2 or 3 react with methyl 3,3-dimethoxypropanoate (1) yielding the corresponding β- ketosulfoxides 4 and 5 respectively. The presence of two methoxy groups in the δ-position of these β-ketosulfoxides has little or no influence on the stereoselectivity of DIBAL and DIBAL/ZnX₂ reductions, allowing the synthesis of the title acetals in high diastereoisomeric excess.