Efficient synthesis of chiral β- and γ-N-tosylaminoalcohols from 1-aryl-2-aminopropane-1,3-diols

(1S,2S)-1-Aryl-2-tozylaminopropan-1-ols were synthesized by cyclization of 1-aryl-2-aminopropane-1,3-diol to aryl(1-tosylaziridin-2-yl)methanols, followed by hydride reduction of the latter. Reduction of the aza-Payne rearrangement products of intermediate aryl(1-tosylaziridin-2-yl)methanols gave (1S)-1-aryl-3-tosylaminopropan-1-ols.