Synlett 1995; 1995(3): 235-237
DOI: 10.1055/s-1995-4921
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Regioselective Cyanide Ring Opening of C2 Symmetric Bis-Aziridines by Cyanide

Juliette Fitremann, Annie Duréault* , Jean-Claude Depezay
  • *Université René Descartes, Laboratoire de Chimie et Biochimie Pharmacologiques et Toxicologiques associé au CNRS, 45 rue des Saints-Pères, 75270 Paris Cedex 06, France
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Publikationsverlauf

Publikationsdatum:
31. Dezember 2000 (online)

The ring-opening of conformationally flexible D-mannitol derived bis-aziridines by cyanide is highly dependent on the reagent and catalytic activation. Cleavage by Me3SiCN under Yb(CN)3 catalysis gives a bis β-aminonitrile of C2 symmetry, ring-opening with NaCN yields a polyhydroxylated pyrrolidine of D-gluco configuration, whereas the Et2AlCN mediated reaction leads to a cyano substituted piperidine of D-manno configuration in addition to the latter azafuranose.