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Catalytic stereodivergent allylic alkylation of 2-acylimidazoles for natural product synthesis

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  • Ruimin Lu

    (University of Science and Technology of China)

  • Qinglin Zhang

    (University of Science and Technology of China)

  • Chang Guo

    (University of Science and Technology of China)

Abstract

The stereocontrolled allylic alkylation of carbonyl compounds with the goal of producing the full range of stereoisomers presents an effective approach for increasing the productivity of collective natural product synthesis and the creation of chiral molecule libraries for drug exploration. The simultaneous control of regio-, diastereo-, and enantioselectivity poses a significant synthetic challenge in contemporary organic synthesis. Herein, we describe a catalytic stereodivergent α-allylation protocol applicable to both aliphatic and aromatic 2-acylimidazoles, thereby providing a practical blueprint for the divergent synthesis of important chiral building blocks. Each of the six isomeric α-allylated compounds can be readily obtained with remarkable yields and exceptional stereoselectivities, by judiciously selecting the appropriate leaving group and permutations of enantiomers adapted from nickel and iridium catalysts. The versatility of this asymmetric allylic alkylation has been successfully utilized in the enantioselective synthesis of (R)-arundic acid and (S,S)-cinamomumolide, as well as in the stereodivergent total synthesis of tapentadol.

Suggested Citation

  • 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.
  • Handle: RePEc:nat:natcom:v:14:y:2023:i:1:d:10.1038_s41467-023-43986-6
    DOI: 10.1038/s41467-023-43986-6
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    References listed on IDEAS

    as
    1. Yu-Hua Wen & Zi-Jing Zhang & Shuai Li & Jin Song & Liu-Zhu Gong, 2022. "Stereodivergent propargylic alkylation of enals via cooperative NHC and copper catalysis," Nature Communications, Nature, vol. 13(1), pages 1-10, December.
    2. 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.
    3. Shi-Ming Xu & Liang Wei & Chong Shen & Lu Xiao & Hai-Yan Tao & Chun-Jiang Wang, 2019. "Stereodivergent assembly of tetrahydro-γ-carbolines via synergistic catalytic asymmetric cascade reaction," Nature Communications, Nature, vol. 10(1), pages 1-11, December.
    4. 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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