Beilstein J. Org. Chem.2022,18, 991–998, doi:10.3762/bjoc.18.99
at room temperature resulted in 3,3-dicyano-5-hydroxy-5-arylcyclopent-1-ene-1,2-dicarboxylates in high yields. More importantly, the DABCO-promoted domino reaction of two molecules of each phenacylmalononitrile and dialkyl but-2-ynedioate in acetonitrile at room temperature afforded unique
multifunctionalized carboxamide-bridged dicyclopentenes in moderate to good yields and with high diastereoselectivity.
Keywords: carboxamide; cycloaddition; cyclopentene; electron-deficient alkyne; phenacylmalononitrile; Introduction
Phenacylmalononitrile is one of the privileged functionalized compounds [1][2][3
][4][5], because it contains one carbonyl group, two cyano groups, and an activated methylene unit. Phenacylmalononitrile exhibits versatile reactivity, high synthetic efficiency and molecular diversity and has been widely employed in many synthetic reactions [6][7][8][9][10]. On the other hand
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Graphical Abstract
Scheme 1:
Representative cycloaddition reactions of phenacylmalononitriles.