NITROMETHANE ADDITION TO ALDOSES PROMOTED BY STRONGLY BASIC ANION-EXCHANGE RESIN IN THE OH- FORM

1-Deoxy-1-nitroalditols can be readily obtained by one-pot reaction of aldoses with nitromethane in aqueous methanol in the presence of a st rongly basic anion-exchange resin in the OH- form and subsequent trans formation of the resin into the HCO3- form with dry ice. All D-pentose s and six available D-hexoses gave moderate to high conversions (48-91 %) to the nitroaldol products, mostly both epimeric 1-deoxy-1-nitroal ditols, in some cases accompanied by tautomeric 2,5- and 2,6-anhydro-1 -deoxy-1-nitroalditols . Both types of the strongly basic anion-exchan ge resins used, R-CH(2)N(+)Me(3) OH- and R-CH(2)N(+)Me(2)(CH2CH2OH) OH - showed comparable catalytic efficiency. Examples of preparation of 1 -deoxy-1-nitro-L-mannitol and -L-glucitol as well as L-mannose and L-g lucose show a practical application of the procedure.