A convergent, stereocontrolled synthesis of C2-symmetrical and pseudosymmetrical sulfur-tethered bis(amino alcohols)

Article abstract of DOI:10.1016/S0040-4039(99)00568-7

The totally enantiocontrolled preparation of C₂-symmetrical and pseudosymmetrical sulfur-tethered bis(amino alcohols) from anti-3-amino-1,2- alkane diols is described. The key step in the synthetic procedure involves the use of triphenylsilanethiol as a sulfide or hydrogenosulfide equivalent in the regioselective nucleophilic ring opening of both anti- and syn- aminoalkyl epoxides.