Home > Research > Publications & Outputs > Investigation of the palladium-catalysed cyclis...

Electronic data

  • Franckevicius Tetrahedron Dihydrooxazines Accepted Version

    Rights statement: 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

    Accepted author manuscript, 938 KB, PDF document

    Available under license: CC BY-NC-ND: Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License

Links

Text available via DOI:

View graph of relations

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

Research output: Contribution to journalJournal articlepeer-review

Published
Close
Article number131866
<mark>Journal publication date</mark>29/01/2021
<mark>Journal</mark>Tetrahedron
Volume80
Number of pages16
Publication StatusPublished
Early online date10/12/20
<mark>Original language</mark>English

Abstract

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.

Bibliographic note

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