Design and development of a new class of strained 2,3-methyleneoxetanes

ORGN 646

Amy R. Howell and Ravinder Raju. Department of Chemistry, University of Connecticut, Storrs, CT 06269
The conversion of 3-alkylidene-2-methyleneoxetanes to 1,5-dioxapiro[3.2]hexanes and enynols has confirmed the potential of these oxetanes as synthetic scaffolds. The utility of these strained monocyclic systems has encouraged us to focus on the preparation of bicyclic 3-alkylidene-2-methyleneoxetanes, 3. Toward this goal, we have prepared Baylis-Hillman adduct 1, which upon by ring closing metathesis with second generation Grubbs catalyst afforded 2. We anticipate the successful formation of 3 by employing methodology previously developed by our group. Preliminary investigations of the reactivity and utility of 3 will be discussed.