Journal of Organic Chemistry p. 10306 - 10320 (2019)
Update date:2022-08-15
Topics:
Bulandr, Jacob J.
Grabowski, Jacob P.
Law, Chunyin M.
Shaw, Jessica L.
Goodell, John R.
Mitchell, T. Andrew
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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