I. Mccort et al., PRACTICAL ROUTE TO D-MANNO AND D-GLUCO AZASUGARS FROM C-2 SYMMETRICALBIS-AZIRIDINES, Tetrahedron letters, 37(43), 1996, pp. 7717-7720
6-Amino-2,5-imino-D-glucitol 2 and 6-amino-1,5-imino-D-mannitol 3, sub
stituted by a free hydroxyl group, have been synthesized from the conf
ormationally flexible N-Boc bis-aziridine 1. Regioselective ring-openi
ng of 1 by acetic acid is a straight way towards 2, while reaction of
1 with water or allylic alcohol under ytterbium triflate catalysis pro
duces selectively the azapyranose 3. Nitrous deamination carried out o
n the cyclic carbamate-protected pyrrolidine 4 leads to a 1:1 mixture
of both 2,5-imino-D-glucitols 5 and 6 bearing a free hydroxyl substitu
ent either at C-1 or at C-6. Copyright (C) 1996 Published by Elsevier
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