Systematic investigation of intramolecular
silyloxypyrone-based
[5 + 2] cycloadditions revealed three significant factors impacting
conversion to cycloadduct: (1) the silyl transfer group has a substantial
influence on the rate of reaction, and the robust t-butyldiphenylsilyl group was found to be more effective overall
than the conventional t-butyldimethylsilyl group;
(2) α,β-unsaturated esters were generally more reactive
than terminal olefins and afforded appreciable quantity of cycloadduct
even at room temperature; and (3) the proximity of the tether to the
silyl transfer group revealed a critical alignment trend between the
pyrone and the alkene. Taken together, these investigations provided
insight regarding the steric and electronic parameters that impact
the scope and limitation of these reactions.
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