Regioselective Cyanide Ring Opening of C2 Symmetric Bis-Aziridines by Cyanide
- 1 March 1995
- journal article
- letter
- Published by Georg Thieme Verlag KG in Synlett
- Vol. 1995 (03) , 235-237
- https://doi.org/10.1055/s-1995-4921
Abstract
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.Keywords
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