Fragmentation of carbohydrate anomeric alkoxy radicals: a new synthesis of chiral 1-halo-1-bromo compounds |
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Authors: | Concepció n C Gonzá lezElisa I Leó n,Concepció n Riesco-FagundoErnesto Suá rez |
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Abstract: | The reaction of 1,2-halohydrins derived from easily available carbohydrates with (diacetoxyiodo)benzene (DIB) in the presence of bromine is a mild procedure for the synthesis of 1-deoxy-1-halo-1-bromo-alditols with one carbon less than the original carbohydrate. The reaction goes through β-fragmentation of the intermediate anomeric alkoxyl radicals. These 1-halo-1-bromo polyhydroxy compounds may be valuable synthetic intermediates in organic synthesis. |
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