Back to Search Start Over

Copper(II) Triflate As a Reusable Catalyst for the Synthesis of trans-4,5-Diamino-cyclopent-2-enones in Water.

Authors :
Gomes RFA
Esteves NR
Coelho JAS
Afonso CAM
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