Synthesis of enantiomerically pure 1,3-diols by stereoselective reduction of β-ketosulfoxides. Influence of a stereogenic hydroxylic centre at the δ-position

Article abstract of DOI:10.1016/S0957-4166(97)00437-0

The influence of the stereogenic hydroxylic carbon at the δ-position of the carbonyl group in 1,5-bis(p-tolylsulfinyl)-4-hydroxy-2-pentanone 1 and 2,6-bis(p-tolylsulfinyl)-5-hydroxy-3-hexanones 2 on the stereochemical course of DIBALH and DIBALH/ZnBr₂ reductions has been studied. In contrast with the DIBALH reductions of β-hydroxyketones, that are monitored by the hydroxylic stereogenic carbon, the presence of the sulfinyl group determines a complete 1,3-induction of the sulfur centre.