Investigation of the palladium-catalysed cyclisation of α-amido malonates with propargylic compounds

Barlow, Sean and Callaghan, Lily and Franckevicius, Vilius (2021) Investigation of the palladium-catalysed cyclisation of α-amido malonates with propargylic compounds. Tetrahedron, 80: 131866. ISSN 0040-4020

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The palladium-catalysed cyclisation of propargylic electrophiles with nucleophiles represents a useful synthetic approach for the rapid construction of heterocyclic building blocks. However, these cyclisation reaction processes often pose a number of challenges due to the need for the simultaneous control of chemo-, regio- and stereoselectivity. Herein, we disclose the discovery of α-amido malonates as novel bis-nucleophiles in the highly chemo- and regioselective, as well as moderately enantioselective, palladium-catalysed cyclisation with propargylic compounds to afford a broad range of functionalised dihydrooxazine heterocycles. The new dihydrooxazine products will expand the suite of heterocycles available to medicinal chemists, and prompt the investigation of unchartered bis-nucloeophiles in palladium-catalysed cyclisation reactions en route to novel classes of heterocycle.

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This is the author’s version of a work that was accepted for publication in Tetrahedron. Changes resulting from the publishing process, such as peer review, editing, corrections, structural formatting, and other quality control mechanisms may not be reflected in this document. Changes may have been made to this work since it was submitted for publication. A definitive version was subsequently published in Tetrahedron, 80, 2021 DOI: 10.1016/j.tet.2020.131866
Uncontrolled Keywords:
?? palladium catalysispropargylic compoundscyclisationheterocyclesdihydrooxazinesbiochemistryorganic chemistrydrug discovery ??
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04 Jan 2021 13:25
Last Modified:
15 Jul 2024 21:18