Flexible and stereoselective construction of polypropionate chains from enantiomerically pure γ-hydroxy-α,β-unsaturated sulfones

Article abstract of DOI:10.1016/S0040-4020(01)90483-1

Following an homologation sequence the readily available enantiomerically pure γ-hydroxy vinyl sulfone 2 has been transformed, with complete control of the stereochemistry, into γ-hydroxy vinyl sulfones of polypropionate structure. The four stereotriads have been prepared by stereoselective additions of organometallics to the vinyl sulfone moiety and by stereoselective reduction of β-hydroxyketones. In a similar way, these triads are the substrates for the stereoselective introduction of the fourth consecutive asymmetric center.