INVESTIGATION OF SILYLOXYPYRONE-ALKENE [5+2] CYCLOADDITIONS
T. Andrew Mitchell
Studies of intramolecular silyloxypyrone-based [5+2] cycloadditions revealed three significant factors impacting conversion to cycloadduct: 1) the more robust t-butyldiphenylsilyl (i.e. TBDPS) transfer group was found to be significantly more effective than the conventional t-butyldimethylsilyl (i.e. TBS) group; 2) α,β-unsaturated esters were more reactive than terminal olefins demonstrating trace conversion even at room temperature; and 3) the proximity of the intramolecular tether to the silyl transfer group revealed a critical alignment trend. These investigations provided insight regarding the steric and electronic parameters of this useful reaction leading to improvements for the intermolecular variants.
Bulandr, Jacob, "INVESTIGATION OF SILYLOXYPYRONE-ALKENE [5+2] CYCLOADDITIONS" (2019). University Research Symposium. 308.