Thermolysis of ω-iodoalkyl-β-siloxyalkenenitriles
in
DMSO triggers an oxidative cyclization cascade that affords highly
oxygenated hydrindanones, decalones, and undecanones. The cyclization
cascade is highly unusual on three counts: the cyclization installs
a contiguous array of tertiary–quaternary–tertiary centers,
thermolysis equilibrates a quaternary center, and the enolsilyl ether
crossed-aldol proceeds without a catalyst.
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