REGIOSELECTIVE CYANIDE RING-OPENING OF C-2 SYMMETRICAL BIS-AZIRIDINESBY CYANIDE

The ring-opening of conformationally flexible D-mannitol derived bis-a ziridines by cyanide is highly dependent on the reagent and catalytic activation. Cleavage by Me(3)SiCN under Yb(CN)(3) catalysis gives a bi s beta-aminonitrile of C-2 symmetry, ring-opening with NaCN yields a p olyhydroxylated pyrrolidine of D-gluco configuration, whereas the Et(2 )AlCN mediated reaction leads to a cyano substituted piperidine of D-m anno configuration in addition to the latter azafuranose.