Cyclobutenone as a highly reactive dienophile: expanding upon Diels-Alder paradigms.
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.
Li
Xiaohua
X
Department of Chemistry, Columbia University, Havemeyer Hall, 3000 Broadway, New York, New York 10027, USA.
Danishefsky
Samuel J
SJ
D000475:Alkenes / Q000737:chemistry*; D002074:Butanones / Q000737:chemistry*; D003500:Cyclization; D003503:Cyclobutanes / Q000737:chemistry*
D000475:Alkenes; D002074:Butanones; D003503:Cyclobutanes; C553737:cyclobutenone