Annulation of enals with carbamoylpropiolates via NHC-catalyzed enolate pathway: access to functionalized maleimides/iso-maleimides and synthesis of aspergillus FH-X-213

TitleAnnulation of enals with carbamoylpropiolates via NHC-catalyzed enolate pathway: access to functionalized maleimides/iso-maleimides and synthesis of aspergillus FH-X-213
Publication TypeJournal Article
Year of Publication2021
AuthorsViveki, AB, Pol, MD, Halder, P, Sonavane, SR, Mhaske, SB
JournalJournal of Organic Chemistry
Volume86
Issue14
Pagination9466-9477
Date PublishedJUL
Type of ArticleArticle
ISSN0022-3263
AbstractHerein 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.
DOI10.1021/acs.joc.1c00782
Type of Journal (Indian or Foreign)Foreign
Impact Factor (IF)4.354
Divison category: 
Organic Chemistry

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