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Cyclobutenone as a Highly Reactive Dienophile: Expanding Upon Diels−Alder Paradigms

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posted on 18.08.2010, 00:00 by Xiaohua Li, Samuel J. Danishefsky
Cyclobutenone was employed as a dienophile in Diels−Alder cycloadditions, provide diverse and complex cycloadducts in good yields. Experimental outcomes indicated cyclobutenone to be more reactive than either cyclopentenone or cyclohexenone. In addition, cycloadducts bearing a strained cyclobutanone moiety were able to undergo regioselective ring expansions to produce corresponding cyclopentanones, lactones, and lactams, which are otherwise difficultly obtained by direct Diels−Alder reactions.

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