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
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Final published version
Research output: Contribution to Journal/Magazine › Journal article › peer-review
Research output: Contribution to Journal/Magazine › Journal article › peer-review
}
TY - JOUR
T1 - Investigation of the palladium-catalysed cyclisation of α-amido malonates with propargylic compounds
AU - Barlow, Sean
AU - Callaghan, Lily
AU - Franckevicius, Vilius
N1 - 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
PY - 2021/1/29
Y1 - 2021/1/29
N2 - 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.
AB - 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.
KW - Palladium catalysis
KW - Propargylic compounds
KW - Cyclisation
KW - Heterocycles
KW - Dihydrooxazines
U2 - 10.1016/j.tet.2020.131866
DO - 10.1016/j.tet.2020.131866
M3 - Journal article
VL - 80
JO - Tetrahedron
JF - Tetrahedron
SN - 0040-4020
M1 - 131866
ER -