Annulation of enals with carbamoylpropiolates via NHC-catalyzed enolate pathway: access to functionalized maleimides/iso-maleimides and synthesis of aspergillus FH-X-213
| Title | Annulation of enals with carbamoylpropiolates via NHC-catalyzed enolate pathway: access to functionalized maleimides/iso-maleimides and synthesis of aspergillus FH-X-213 |
| Publication Type | Journal Article |
| Year of Publication | 2021 |
| Authors | Viveki, AB, Pol, MD, Halder, P, Sonavane, SR, Mhaske, SB |
| Journal | Journal of Organic Chemistry |
| Volume | 86 |
| Issue | 14 |
| Pagination | 9466-9477 |
| Date Published | JUL |
| Type of Article | Article |
| ISSN | 0022-3263 |
| Abstract | 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. |
| DOI | 10.1021/acs.joc.1c00782 |
| Type of Journal (Indian or Foreign) | Foreign |
| Impact Factor (IF) | 4.354 |
Divison category:
Organic Chemistry