Unique reactivity of anti- and syn-acetoxypyranones was observed in oxidopyrylium-alkene [5 + 2] cycloadditions. The subtle interplay between the corresponding acetoxypyranone conformation and steric bulk of tertiary amine bases causes syn-acetoxypyranones to undergo [5 + 2] cycloaddition appreciably faster than anti-acetoxypyranones. As a result of these investigations, several cascade processes that afford novel caged ethers have been observed.

Novel cascade reactions discovered from investigation of acetoxypyranone-derived oxidopyrylium [5+2] cycloadditions

247th National Meeting (2014)

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