Back to Search
Start Over
Phosphine-Catalyzed Annulations of 4,4-Dicyano-2-Methylenebut-3-enoates with Maleimides and Maleic Anhydride.
- Source :
-
Angewandte Chemie . Sep2014, Vol. 126 Issue 40, p10944-10949. 6p. - Publication Year :
- 2014
-
Abstract
- A novel phosphine-catalyzed [4+1] annulation of maleimides with 4,4-dicyano-2-methylenebut-3-enoates has been developed to afford spirocyclic products, and the maleimides serves as C1 synthons. Moreover, a phosphine-catalyzed formal [3+2] annulation between 4,4-dicyano-2-methylenebut-3-enoates and maleic anhydride has been also achieved, and maleic anhydride behaved as a C3 synthon in the reaction, thus efficiently affording the functionalized cyclopentenones. A stable phosphinium-containing zwitterionic compound is the key reactive intermediate in both annulations and was successfully isolated. Plausible mechanisms have been proposed on the basis of control experiments and deuterium-labeling experiments. [ABSTRACT FROM AUTHOR]
- Subjects :
- *MALEIMIDES
*ANNULATION
*CATALYSTS
*PHOSPHINE
*ZWITTERIONS
*DEUTERIUM
Subjects
Details
- Language :
- English
- ISSN :
- 00448249
- Volume :
- 126
- Issue :
- 40
- Database :
- Academic Search Index
- Journal :
- Angewandte Chemie
- Publication Type :
- Academic Journal
- Accession number :
- 98420316
- Full Text :
- https://doi.org/10.1002/ange.201406100