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Catalytic asymmetric Tsuji–Trost α−benzylation reaction of N-unprotected amino acids and benzyl alcohol derivatives

Author

Listed:
  • Jian-Hua Liu

    (School of Chemistry and Chemical Engineering, Southwest University)

  • Wei Wen

    (School of Chemistry and Chemical Engineering, Southwest University)

  • Jian Liao

    (School of Chemistry and Chemical Engineering, Southwest University)

  • Qi-Wen Shen

    (School of Chemistry and Chemical Engineering, Southwest University)

  • Yao Lin

    (School of Chemistry and Chemical Engineering, Southwest University)

  • Zhu-Lian Wu

    (School of Chemistry and Chemical Engineering, Southwest University)

  • Tian Cai

    (School of Chemistry and Chemical Engineering, Southwest University)

  • Qi-Xiang Guo

    (School of Chemistry and Chemical Engineering, Southwest University)

Abstract

Catalytic asymmetric Tsuji–Trost benzylation is a promising strategy for the preparation of chiral benzylic compounds. However, only a few such transformations with both good yields and enantioselectivities have been achieved since this reaction was first reported in 1992, and its use in current organic synthesis is restricted. In this work, we use N-unprotected amino acid esters as nucleophiles in reactions with benzyl alcohol derivatives. A ternary catalyst comprising a chiral aldehyde, a palladium species, and a Lewis acid is used to promote the reaction. Both mono- and polycyclic benzyl alcohols are excellent benzylation reagents. Various unnatural optically active α-benzyl amino acids are produced in good-to-excellent yields and with good-to-excellent enantioselectivities. This catalytic asymmetric method is used for the formal synthesis of two somatostatin mimetics and the proposed structure of natural product hypoestestatin 1. A mechanism that plausibly explains the stereoselective control is proposed.

Suggested Citation

  • Jian-Hua Liu & Wei Wen & Jian Liao & Qi-Wen Shen & Yao Lin & Zhu-Lian Wu & Tian Cai & Qi-Xiang Guo, 2022. "Catalytic asymmetric Tsuji–Trost α−benzylation reaction of N-unprotected amino acids and benzyl alcohol derivatives," Nature Communications, Nature, vol. 13(1), pages 1-11, December.
    • Handle: RePEc:nat:natcom:v:13:y:2022:i:1:d:10.1038_s41467-022-30277-9
    DOI: 10.1038/s41467-022-30277-9
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    1. Wei Wen & Ming-Jing Luo & Yi Yuan & Jian-Hua Liu & Zhu-Lian Wu & Tian Cai & Zhao-Wei Wu & Qin Ouyang & Qi-Xiang Guo, 2020. "Diastereodivergent chiral aldehyde catalysis for asymmetric 1,6-conjugated addition and Mannich reactions," Nature Communications, Nature, vol. 11(1), pages 1-11, December.
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    Cited by:

    1. Fang Zhu & Chao-Xing Li & Zhu-Lian Wu & Tian Cai & Wei Wen & Qi-Xiang Guo, 2022. "Chiral aldehyde-nickel dual catalysis enables asymmetric α−propargylation of amino acids and stereodivergent synthesis of NP25302," Nature Communications, Nature, vol. 13(1), pages 1-9, December.

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    1. Fang Zhu & Chao-Xing Li & Zhu-Lian Wu & Tian Cai & Wei Wen & Qi-Xiang Guo, 2022. "Chiral aldehyde-nickel dual catalysis enables asymmetric α−propargylation of amino acids and stereodivergent synthesis of NP25302," Nature Communications, Nature, vol. 13(1), pages 1-9, December.

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