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A new class of highly regio- and stereoselective intramolecular rearrangements of glycidol acetals to produce alkoxylated 1,3-dioxolane/1,3-dioxane is demonstrated. Selective Lewis acid activation of acetal generates an oxocarbenium ion that… Click to show full abstract
A new class of highly regio- and stereoselective intramolecular rearrangements of glycidol acetals to produce alkoxylated 1,3-dioxolane/1,3-dioxane is demonstrated. Selective Lewis acid activation of acetal generates an oxocarbenium ion that initiates the epoxide ring-opening event, giving the bicyclic [3,1,0]epoxonium ion intermediate that undergoes exo/endo-selective opening by a tethered alkoxide. Mechanistic insights into preferential acetal activation over the epoxide were obtained by crossover experiments. The method was applied in the total synthesis of parvistone B and its 8-ethoxy analogue.
Journal Title: Organic letters
Year Published: 2022
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