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Cyclobutenone as a highly reactive dienophile: expanding upon Diels-Alder paradigms.

ABSTRACT: 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.

SUBMITTER: Li X

PROVIDER: S-EPMC2956739 | biostudies-literature | 2010 Aug

REPOSITORIES: biostudies-literature

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Cyclobutenone as a highly reactive dienophile: expanding upon Diels-Alder paradigms.

Li Xiaohua X Danishefsky Samuel J SJ

Journal of the American Chemical Society 20100801 32

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. ...[more]

PMID: 20698657

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