INVESTIGATION OF SILYLOXYPYRONE-ALKENE [5+2] CYCLOADDITIONS
Publication Date
4-5-2019
Document Type
Poster
Degree Type
Undergraduate
Department
Chemistry
Mentor
T. Andrew Mitchell
Mentor Department
Chemistry
Abstract
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.
Recommended Citation
Bulandr, Jacob, "INVESTIGATION OF SILYLOXYPYRONE-ALKENE [5+2] CYCLOADDITIONS" (2019). University Research Symposium. 308.
https://ir.library.illinoisstate.edu/rsp_urs/308