The alkylation of a novel acetal derived from (2R,3R)-(+)-tartaric acid: An unexpected rearrangement

Article abstract of DOI:10.1016/S0040-4039(98)02650-1

The novel chiral bis-acetal dioxane 2a derived from (2R,3R)-(+)-tartaric acid was shown to undergo an unexpected rearrangement upon treatment with lithium amide base to give the chiral dioxolane 3a in optically active form. Alkylation and aldol studies were performed on the diisopropyl ester of this dioxolane 3b.