Synthesis of chiral amino epoxyaziridines: useful intermediates for the preparation of chiral trisubstituted piperidines.
Chiral aminoalkyl epoxyaziridine 1 is synthesized in high yield and diastereoselectivity from L-serine. Ring opening of epoxyaziridine 1 with primary amines is carried out with total chemo- and regioselectivity, affording chiral polyfunctionalized piperidines 8. The structure of these trisubstituted piperidines is established by NMR studies.
Concellón
José M
JM
Departamento de Química Orgánica e Inorgánica, Facultad de Química, Universidad de Oviedo, Julián Clavería 8, 33071 Oviedo, Spain. jmcg@sauron.quimica.uniovi.es
Riego
Estela
E
Rivero
Ignacio A
IA
Ochoa
Adrián
A