1,3-dipolar cycloaddition reactions of homochiral cyclic nitrones derived from 1-deoxynojirimycin

The synthesis of nitrones 12, 19 and 20, derived from 1-deoxynojirimycin (1, dNM), using 2,2-dimethyldioxirane, is reported. In subsequent 1,3-dipolar cycloaddition reactions of nitrones 12 and 19 with phenyl isocyanate and trichloro acetonitrile the cycloadducts 13 and 15, ring-closed to C-1, and 14, 16, 21 and 22, which are ring-closed to C-5 of the dNM ring, were obtained. Cycloaddition reaction of 19 and 20 with methyl vinylacetate at 15 kbar pressure, provided the cycloadducts 23, 24 and 25, which are highly functionalized dNM derivatives with various possibilities for further synthesis.