Stereoselective synthesis of 3-alkylsulfinylmethylisoxazolines and their use as chiral nucleophiles in the chain elongation of 2,3-O-isopropylidene-D-glyceraldehyde

Article abstract of DOI:10.1016/S0957-4166(00)00453-5

The reaction of racemic 3-methylisoxazolines and enantiomerically pure (R_S)- and (S_S)-methanesulfinates and (R_S)- and (S_S)-ethanesulfinates of 1,2:5,6-di-O-isopropylidene-D-glucofuranose allows enantiomerically pure 3-alkylsulfinylmethylisoxazolines with both absolute configurations at sulfur to be obtained. One of these has been used as a chiral nucleophile in the four carbon homologation of 2,3-O-isopropylidene-D-glyceraldehyde 17.