Synthesis of Chiral Amino Epoxyaziridines:  Useful Intermediates
for the Preparation of Chiral Trisubstituted Piperidines

Concellón, José M.; Riego, Estela; Rivero, Ignacio A.; Ochoa, Adrián

doi:10.1021/jo0490806.s001

Synthesis of Chiral Amino Epoxyaziridines: Useful Intermediates for the Preparation of Chiral Trisubstituted Piperidines

journal contribution

posted on 2004-09-17, 00:00 authored by José M. Concellón, Estela Riego, Ignacio A. Rivero, Adrián Ochoa

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.