Physical Sciences and Mathematics Commons^™

New Reactions Of Ring Strained Allyl Silanes, Elizabeth J. (Elizabeth Jane) Cummins

WWU Graduate School Collection

Herein, we report new allylation reactions using ring-strained allylalkoxysiletanes. These reactions can achieve high yield and have high chemoselectivity, as evidenced by carefully designed substrates. Based on previous evidence, we propose that the reaction proceeds through an exchange mechanism, where first the alkoxy group of the siletane exchanges with the hydroxyl group of the substrate, followed by coordination of the substrate carbonyl to the siletane, and then intramolecular allylation of the carbonyl.