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Issue 29, 2018
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Phosphine-catalysed α-umpolung addition of nucleophiles to δ-acetoxy allenoates: stereoselective synthesis of 2,4-dienoates

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Abstract

The first example of phosphine-catalyzed α-umpolung addition of nucleophiles to allenoates is described, which features the use of δ-acetoxy allenoate to generate a 3-phosphonium-2,4-dienoate intermediate, thus facilitating the α-umpolung addition of nucleophiles. Both sulfinate and diarylphosphine oxide are competitive nucleophiles, affording highly activated conjugated dienes with good to excellent stereoselectivities.

Graphical abstract: Phosphine-catalysed α-umpolung addition of nucleophiles to δ-acetoxy allenoates: stereoselective synthesis of 2,4-dienoates

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Publication details

The article was received on 20 Apr 2018, accepted on 06 Jun 2018 and first published on 07 Jun 2018


Article type: Communication
DOI: 10.1039/C8OB00933C
Citation: Org. Biomol. Chem., 2018,16, 5245-5249
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    Phosphine-catalysed α-umpolung addition of nucleophiles to δ-acetoxy allenoates: stereoselective synthesis of 2,4-dienoates

    Y. Hou, Y. Zhang and X. Tong, Org. Biomol. Chem., 2018, 16, 5245
    DOI: 10.1039/C8OB00933C

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