Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 22, Issue 1, Pages 144-152Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201503742
Keywords
C-H activation; lactones; microreactors; palladium; photochemistry
Categories
Funding
- Ministerio de Economia y Competitividad (MINECO) (Spain) [CTQ2011-22589, CTQ2011-22410, CTQ2013-40855-R, CTQ2014-54987-P]
- Gobierno de Aragon-Fondo Social Europeo (Spain) [E40, E97]
- Ministerio de Economia y Competitividad (Spain)
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The stereoselective synthesis of epsilon-isomers of dimethyl esters of 1,3-diaminotruxillic acid in three steps is reported. The first step is the ortho-palladation of (Z)-2-aryl-4aryliden-5(4H)-oxazolones 1 to give dinuclear complexes 2 with bridging carboxylates. The reaction occurs through regioselective activation of the ortho-C-H bond of the 4-arylidene ring in carboxylic acids. The second step is the [2+2]photocycloaddition of the C=C exocyclic bonds of the oxazolone skeleton in 2 to afford the corresponding dinuclear ortho-palladated cyclobutanes 3. This key step was performed very efficiently by using LED light sources with different wavelengths 9465, 525 or 625 nm) in flow microreactors. The final step involved the depalladation of 3 by hydrogenation in methanol to afford the epsilon-1,3-diaminotruxillic acid derivatives as single isomers.
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