Abstract
Abstract A simple and convenient method for the synthesis of cyclopropanes substituted with carbohydrate analogues is described. The addition of trifluoromethyl diazo compounds to 5-(R)-hydroxypyridazin-3-one derivative of d -(+)-galactose proceeded in almost quantitative yields and high syn -selectivity. The observed π-facial selectivity is determined by the configuration at C-5. The exo -selectivity was complete in all the cases. Steric interactions and electronic factors seem to be the main ones responsible for the observed exo selectivity and π-facial selectivity of reactions with trifluoromethyl diazo compounds.
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