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Copper(II) Triflate As a Reusable Catalyst for the Synthesis of trans-4,5-Diamino-cyclopent-2-enones in Water.
- Source :
-
The Journal of organic chemistry [J Org Chem] 2018 Jul 20; Vol. 83 (14), pp. 7509-7513. Date of Electronic Publication: 2018 Feb 09. - Publication Year :
- 2018
-
Abstract
- trans-4,5-Diamino-cyclopent-2-enones (CP) are usually prepared by Lewis acid-catalyzed condensation of furfural and a secondary amine in an organic solvent. The reaction proceeds through the formation of a Stenhouse salt (SS) intermediate followed by an electrocyclization reaction to afford the desired CP. Herein, we described the use of Cu(OTf) <subscript>2</subscript> as a very efficient catalyst for the synthesis of CP in water at room temperature. Furthermore, the mild reaction conditions, catalyst reusability, and outstanding functional group tolerance suggest that this CP platform can be further used in chemical biology.
Details
- Language :
- English
- ISSN :
- 1520-6904
- Volume :
- 83
- Issue :
- 14
- Database :
- MEDLINE
- Journal :
- The Journal of organic chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 29400462
- Full Text :
- https://doi.org/10.1021/acs.joc.7b02931