Wang p-alkoxyphenylsulfoxide as a new linker and Pummerer cleavage strategy in solid-phase preparation of 1,2-diols

para-Hydroxyphenyl-β-ketosulfide was attached to a Wang resin and oxidised to the corresponding sulfoxide with a N-protonated oxaziridinium trifluoroacetate. Reduction of the β-ketosulfoxides to the corresponding β-hydroxysulfoxides with Dibal-H was shown to be as stereoselective as in solution. Finally it was shown that the Pummerer reaction could be carried out on solid-phase and was a very efficient way to obtain diols that validates the sulfoxide group as a versatile linker for solid-phase chemistry.