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

[摘要]：The transformation of enantiopure (2R,4R)- and (2S,4S)-N,N-dibenzyl-1,2:4,5-diepoxypentan-3-amine into the corresponding enantiopure (3S,5S)- and (3R,5R)-3,5-dihydroxy-3-aminopiperidines 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.

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