Tetrahedron p. 2157 - 2170 (1999)
Update date:2022-07-29
Topics:
Rodriguez, Juan B.
1,4-Dicarbonyl-2,3-chiral derivatives are useful synthetic precursors for the preparation of carbocyclic rings but, in many cases, losses of optical purity have been reported. 1-Deoxy-3,4-O-isopropylidene-6-O-trityl- D-erythro-hexo-2,5-diulose and 1-deoxy-3,4-O-isopropylidene-6-O-(tert- butyldiphenylsilyl)-D-erythro-hexo-2,5-diulose were synthesized from D- ribono-1,4-lactone. These compounds were selected to study the epimerizability of 2,3-O-isopropylidene-1,4-dicarbonyl derivatives. It was found that both compounds smoothly epimerize and partially racemize on standing.
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