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Phosphine-Catalysed α-Umpolung Addition of Nucleophiles to δ-Acetoxy Allenoates: Stereoselective Synthesis of 2,4-Dienoate

Abstract

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

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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, Accepted Manuscript
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    Phosphine-Catalysed α-Umpolung Addition of Nucleophiles to δ-Acetoxy Allenoates: Stereoselective Synthesis of 2,4-Dienoate

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

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