从丝氨酸衍生的氨基二环氧物中完全选择性合成对映体纯的(3S,5S)-和(3R,5R)-4-氨基-3,5-二羟基哌啶。

Totally selective synthesis of enantiopure (3S,5S)- and (3R,5R)-4-amino-3,5-dihydroxypiperidines from aminodiepoxides derived from serine.

作者信息

Concellón José M, Rivero Ignacio A, Rodríguez-Solla Humberto, Concellón Carmen, España Estibaly, García-Granda Santiago, Díaz M R

机构信息

Departamento de Química Orgánica e Inorgánica, and Química Física y Analítica, Facultad de Química, Universidad de Oviedo, Julián Clavería 8, 33071 Oviedo, Spain.

出版信息

J Org Chem. 2008 Aug 1;73(15):6048-51. doi: 10.1021/jo801058c. Epub 2008 Jul 4.

DOI:10.1021/jo801058c

PMID:18598082

Abstract

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.

摘要

描述了对映体纯的(2R,4R)-和(2S,4S)-N,N-二苄基-1,2:4,5-二环氧戊烷-3-胺（1和2）分别转化为相应的对映体纯的(3S,5S)-和(3R,5R)-3,5-二羟基-3-氨基哌啶（3和4）的过程。在高氯酸锂存在下，一系列胺与两个环氧环的开环反应具有完全的区域选择性且产率很高。提出了一种解释这种转化的机理。