title: Totally selective synthesis of enantiopure (3S,5S)- and (3R,5R)-4-amino-3,5-dihydroxypiperidines from aminodiepoxides derived from serine.
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.
authors.affiliation: Departamento de Química Orgánica e Inorgánica, and Química Física y Analítica, Facultad de Química, Universidad de Oviedo, Julián Clavería 8, 33071 Oviedo, Spain. jmcg@unioVi.es
authors.forename: José M
authors.initials: JM
authors.lastname: Concellón
authors.forename: Ignacio A
authors.initials: IA
authors.lastname: Rivero
authors.forename: Humberto
authors.initials: H
authors.lastname: Rodríguez-Solla
authors.forename: Carmen
authors.initials: C
authors.lastname: Concellón
authors.forename: Estibaly
authors.initials: E
authors.lastname: España
authors.forename: Santiago
authors.initials: S
authors.lastname: García-Granda
authors.forename: M R
authors.initials: MR
authors.lastname: Díaz
mesh_terms: D000588:Amines / Q000737:chemistry*; D004852:Epoxy Compounds / Q000737:chemistry*; D015394:Molecular Structure; D010880:Piperidines / Q000737:chemistry*; D012694:Serine / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000588:Amines; D004852:Epoxy Compounds; D010880:Piperidines; D012694:Serine