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HOWELL RESEARCH GROUP DEPARTMENT
OF CHEMISTRY |
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Synthesis and Reactivity
of 3-Alkylidene-2-methyleneoxetanes
We have demonstrated that a variety of 3-alkylidene-2-methyleneoxetanes
23, another class of unusual and unexplored strained
heterocycle, can be accessed from alpha-alkylidene-beta-hydroxy esters
22. To date this is the most general approach to this class
of compounds. |
The
conversion of 3-alkylidene-2-methyleneoxetanes to 1,5-dioxapiro[3.2]hexanes
24 and enynols 25 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. |
Toward
this goal, we have prepared Baylis-Hillman adduct 26
and ß-lactone 27. We are currently investigating
the metathesis (RCM and CM) of these strained systems. |
