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Asymmetric α-allylic allenylation of β-ketocarbonyls and aldehydes by synergistic Pd/chiral primary amine catalysis

Author

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  • Chang You

    (Tsinghua University)

  • Mingying Shi

    (Beijing Normal University)

  • Xueling Mi

    (Beijing Normal University)

  • Sanzhong Luo

    (Tsinghua University)

Abstract

We herein describe an asymmetric α-allylic allenylation of β-ketocarbonyls and aldehydes with 1,3-enynes. A synergistic chiral primary amine/Pd catalyst was identified to facilitate the utilization of 1,3-enynes as atom-economic and achiral allene precursors. The synergistic catalysis enables the construction of all-carbon quaternary centers-tethered allenes bearing non-adjacent 1,3-axial central stereogenic centers in high level of diastereo- and enantio-selectivity. By switching the configurations of ligands and aminocatalysts, diastereodivergence can be achieved and any of the four diastereoisomers can be accessed in high diastereo- and enantio- selectivity.

Suggested Citation

  • Chang You & Mingying Shi & Xueling Mi & Sanzhong Luo, 2023. "Asymmetric α-allylic allenylation of β-ketocarbonyls and aldehydes by synergistic Pd/chiral primary amine catalysis," Nature Communications, Nature, vol. 14(1), pages 1-7, December.
    • Handle: RePEc:nat:natcom:v:14:y:2023:i:1:d:10.1038_s41467-023-38488-4
    DOI: 10.1038/s41467-023-38488-4
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    References listed on IDEAS

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    1. Shihua Song & Jing Zhou & Chunling Fu & Shengming Ma, 2019. "Catalytic enantioselective construction of axial chirality in 1,3-disubstituted allenes," Nature Communications, Nature, vol. 10(1), pages 1-9, December.
    2. Shi-Liang Shi & Zackary L. Wong & Stephen L. Buchwald, 2016. "Copper-catalysed enantioselective stereodivergent synthesis of amino alcohols," Nature, Nature, vol. 532(7599), pages 353-356, April.
    3. Thien Phuc Le & Shinji Tanaka & Masahiro Yoshimura & Kazuhiko Sato & Masato Kitamura, 2022. "Stereodivergent dehydrative allylation of β-keto esters using a Ru/Pd synergistic catalyst," Nature Communications, Nature, vol. 13(1), pages 1-10, December.
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    Cited by:

    1. Ruimin Lu & Qinglin Zhang & Chang Guo, 2023. "Catalytic stereodivergent allylic alkylation of 2-acylimidazoles for natural product synthesis," Nature Communications, Nature, vol. 14(1), pages 1-10, December.

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