Solvent-Free Synthesis and Key Intermediate Isolation in Ni 2 Dy 2 Catalyst Development in the Domino Ring-Opening Electrocyclization Reaction of Furfural and Amines

A solvent-free methodology that yields trans-4,5-diaminocyclopent-2-enones, main domains of natural products and a variety of N-heterocycles, is described. The bimetallic catalyst [Ni Dy L (DMF) ] 2(OTf) 2(DMF) (1) promotes the domino reaction of furfural and amines, with loadings as low as 0.01%, u...

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Bibliographic Details
Published in:Journal of organic chemistry 2019-06, Vol.84 (11), p.6858-6867
Main Authors: Sampani, Stavroula I, McGown, Andrew, Vargas, Alfredo, Abdul-Sada, Alaa, Tizzard, Graham J, Coles, Simon J, Spencer, John, Kostakis, George E
Format: Article
Language:English
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Summary:A solvent-free methodology that yields trans-4,5-diaminocyclopent-2-enones, main domains of natural products and a variety of N-heterocycles, is described. The bimetallic catalyst [Ni Dy L (DMF) ] 2(OTf) 2(DMF) (1) promotes the domino reaction of furfural and amines, with loadings as low as 0.01%, under stirring or microwave-assisted conditions to afford the corresponding frameworks in very good to excellent yields. Crystallographic and theoretical studies shed light on the exclusive formation of the trans-diastereoisomers via a 4π-conrotatory electrocyclization process elucidating the key step in the catalytic process.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.9b00608