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

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• 作者：José ; M. Concelló ; n ; Ignacio A. Rivero ; Humberto Rodrí ; guez-Solla ; Carmen Concelló ; n ; Estibaly Españ ; a ; Santiago Garcí ; a-Granda ; M. R. Dí ; az
• 刊名：Journal of Organic Chemistry
• 出版年：2008
• 出版时间：August 1, 2008
• 年：2008
• 卷：73
• 期：15
• 页码：6048-6051
• 全文大小：186K
• 年卷期：v.73,no.15(August 1, 2008)
• ISSN：1520-6904

文摘

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.