Totally Selective Synthesis of Enantiopure (3<i>S</i>,5<i>S</i>)- and (3<i>R</i>,5<i>R</i>)-4-Amino-3,5-dihydroxypiperidines from Aminodiepoxides Derived from Serine

The transformation of enantiopure (2R,4R)- and (2S,4S)-N,N-dibenzyl-1,2:4,5-diepoxypentan-3-amine, 1 and 2, into the corresponding enantiopure (3S,5S)- and (3R,5R)-3,5-dihydroxy-3-aminopiperidines, 3 and 4 respectively, is described. The opening of the two epoxide rings with a range of amines takes place with total regioselectivity and high yields, in the presence of LiClO4. A mechanism to explain this transformation is proposed.