The regioselective and stereospecific substitution of unsymmetrical 1,2-diols using the 1,3,2λ5-dioxaphospholane methodology

Article abstract of DOI:10.1016/S0040-4020(01)96904-2

Stereo specific tosylate (^-OTs) or azide (N₃^-) substitution at the C-4 stereocenter of a monosubstituted 1,3,2λ⁵-dioxaphospholane (the equivalent of the C-2 stereocenter in an unsymmetrical 1,2-diol) is readily achieved by treatment with either P-toluenesulfonic acid (P-TsOH) in tetrahydrofuran solvent or P-TsOH/sodium azide in acetonitrile solvent, respectively.