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Diverse synthesis of α-tertiary amines and tertiary alcohols via desymmetric reduction of malonic esters

Author

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  • Haichao Liu

    (The University of Hong Kong)

  • Vincent Ho Man Lau

    (The University of Hong Kong)

  • Pan Xu

    (The University of Hong Kong)

  • Tsz Hin Chan

    (The University of Hong Kong)

  • Zhongxing Huang

    (The University of Hong Kong)

Abstract

Amines and alcohols with a fully substituted α-carbon are structures of great value in organic synthesis and drug discovery. While conventional methods towards these motifs often rely on enantioselective carbon-carbon or carbon-heteroatom bond formation reactions, a desymmetric method is developed here by selectively hydrosilylating one of the esters of easily accessible α-substituted α-amino- and -oxymalonic esters. The desymmetrization is enabled by a suite of dinuclear zinc catalysts with pipecolinol-derived tetradentate ligands and can accommodate a diverse panel of heteroatom substituents, including secondary amides, tertiary amines, and ethers of different sizes. The polyfunctionalized reduction products, in return, have provided expeditious approaches to enantioenriched nitrogen- and oxygen-containing molecules, including dipeptides, vitamin analogs, and natural metabolites.

Suggested Citation

  • Haichao Liu & Vincent Ho Man Lau & Pan Xu & Tsz Hin Chan & Zhongxing Huang, 2022. "Diverse synthesis of α-tertiary amines and tertiary alcohols via desymmetric reduction of malonic esters," Nature Communications, Nature, vol. 13(1), pages 1-8, December.
    • Handle: RePEc:nat:natcom:v:13:y:2022:i:1:d:10.1038_s41467-022-32560-1
    DOI: 10.1038/s41467-022-32560-1
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    References listed on IDEAS

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    1. Chi Zhang & Zhong-Liang Li & Qiang-Shuai Gu & Xin-Yuan Liu, 2021. "Catalytic enantioselective C(sp3)–H functionalization involving radical intermediates," Nature Communications, Nature, vol. 12(1), pages 1-9, December.
    2. Kazue Yamagishi & Kazuo Onuma & Takashi Suzuki & Fumio Okada & Junji Tagami & Masayuki Otsuki & Pisol Senawangse, 2005. "A synthetic enamel for rapid tooth repair," Nature, Nature, vol. 433(7028), pages 819-819, February.
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