%0 Journal Article %J Journal of Organic Chemistry %D 2021 %T Annulation of enals with carbamoylpropiolates via NHC-catalyzed enolate pathway: access to functionalized maleimides/iso-maleimides and synthesis of aspergillus FH-X-213 %A Viveki, Amol B. %A Pol, Mahesh D. %A Halder, Priyanka %A Sonavane, Sameer R. %A Mhaske, Santosh B. %X Herein we report the N-heterocyclic carbene (NHC)-catalyzed [3 + 2] annulation of alpha,beta-unsaturated aldehydes with carbamoylpropiolates via an unusual enolate pathway leading to the construction of highly functionalized maleimides or isomaleimides. The electronic effect imposed by the alkyl/aryl group present on the amide nitrogen of carbamoylpropiolates plays a crucial role in the selective formation of these important five-membered heterocyclic building blocks. The developed protocol is mild and tolerates a wide range of substituents on both substrates. The application of this protocol in the synthesis of the antibacterial natural product Aspergillus FH-X-213 has also been demonstrated. %B Journal of Organic Chemistry %V 86 %P 9466-9477 %8 JUL %G eng %N 14 %9 Article %3 Foreign %4 4.354 %R 10.1021/acs.joc.1c00782