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

Author(s) Gomes, R.F.A.; Esteves, N.R.; Coelho, J.A.S.; Afonso, C.A.M.
Journal J Org Chem
Date Published 2018 Feb 09

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)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.

DOI 10.1021/acs.joc.7b02931
ISSN 1520-6904
Citation J Org Chem. 2018.

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