SELECTIVE ONE-STEP SYNTHESIS OF ENANTIOPURE CIS-2,5-DISUBSTITUTED PYRROLIDINES OR CIS-3,6-DISUBSTITUTED PIPERIDINES FROM THE (2R,2'R) (1,2-ETHANEDIYL) BIS-AZIRIDINE

Nucleophilic ring opening of the optically active (1,2-ethanediyl) bis -aziridine 1 is dependent on the reagent and solvent. In aprotic mediu m cis-2,5-disubstituted pyrrolidines are formed from the opening of th e aziridine ring at C-l followed by intramolecular 5-exo-tet aminocycl ization. With hydroxylated reagents in protic media, the opening takes place at C-2, leading to 3-hydroxy substituted piperidines via a 6-ex o-tet cyclization process.