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Issue 8, 2019
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Intramolecular hydrogen-bonding-assisted phosphine-catalysed [3 + 2] cyclisation of ynones with o-hydroxy/amino benzaldehydes

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Abstract

A new strategy for the synthesis of functionalized tetrahydrofuran derivatives was developed via a phosphine-catalysed [3 + 2] cyclization reaction of aromatic aldehydes with 4-phenylbut-3-yn-2-one. This is the first example of intermolecular cyclization of ynones with benzaldehydes, which essentially benefited from the intramolecular hydrogen bonding. This new protocol features a broad substrate scope, mild reaction conditions, operational simplicity and easy scale-up.

Graphical abstract: Intramolecular hydrogen-bonding-assisted phosphine-catalysed [3 + 2] cyclisation of ynones with o-hydroxy/amino benzaldehydes

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Publication details

The article was received on 09 Jan 2019, accepted on 24 Jan 2019 and first published on 25 Jan 2019


Article type: Paper
DOI: 10.1039/C9OB00056A
Citation: Org. Biomol. Chem., 2019,17, 2187-2191

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    Intramolecular hydrogen-bonding-assisted phosphine-catalysed [3 + 2] cyclisation of ynones with o-hydroxy/amino benzaldehydes

    Z. Deng, Z. Xie, Y. Zheng, J. Xiao, R. Wang, H. Xiang and H. Yang, Org. Biomol. Chem., 2019, 17, 2187
    DOI: 10.1039/C9OB00056A

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