Totally selective synthesis of enantiopure (3S,5S)- and (3R,5R)-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.
Concellón
José M
JM
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
Rivero
Ignacio A
IA
Rodríguez-Solla
Humberto
H
Concellón
Carmen
C
España
Estibaly
E
García-Granda
Santiago
S
Díaz
M R
MR
D000588:Amines / Q000737:chemistry*; D004852:Epoxy Compounds / Q000737:chemistry*; D015394:Molecular Structure; D010880:Piperidines / Q000737:chemistry*; D012694:Serine / Q000737:chemistry*; D013237:Stereoisomerism
D000588:Amines; D004852:Epoxy Compounds; D010880:Piperidines; D012694:Serine