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.

This document is currently not available here.

Share

COinS