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Catalytic hydrative cyclization of aldehyde-ynamides with water for synthesis of medium-sized lactams

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Abstract

A non-noble metal catalyzed hydrative cyclization of aldehyde-ynamides for efficient and practical synthesis of medium-sized lactams (7- to 9-membered rings) is disclosed. Compared with previous hydrative cyclization for the formation of six-membered lactams (cis-form), a totally inverse diastereoselectivity (trans-form) of medium-sized lactams is observed. In addition, this protocol delivers valuable medium-sized lactams in moderate to good yields with high diastereoselectivities. Moreover, a rational mechanism to understand this inversion of diastereoselectivity is proposed based on theoretical calculations.

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Acknowledgements

This work was supported by the National Natural Science Foundation of China (92056104 and 21772161), the Natural Science Foundation of Fujian Province of China (2019J02001), the President Research Funds from Xiamen University (20720210002), the National Fund for Fostering Talents of Basic Science (NFFTBS) (J1310024), the Opening Project of PCOSS, Xiamen University (201909), the Bioinformatics Center of Nanjing Agricultural University and the Start-up Research Fund of Nanjing Agricultural University (050-804099).

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  1. These authors contributed equally to this work.

Authors and Affiliations

  1. Key Laboratory of Chemical Biology of Fujian Province, State Key Laboratory of Physical Chemistry of Solid Surfaces, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, 361005, China

    Bo-Han Zhu, Yan-Xin Zheng, Wei Kang, Jin-Mei Zhou & Long-Wu Ye

  2. Jiangsu Key Laboratory of Pesticide Science and Department of Chemistry, College of Sciences, Nanjing Agricultural University, Nanjing, 210095, China

    Chao Deng

  3. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, 200032, China

    Long-Wu Ye

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  1. Bo-Han Zhu
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  2. Yan-Xin Zheng
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  3. Wei Kang
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  4. Chao Deng
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  5. Jin-Mei Zhou
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Correspondence to Chao Deng or Long-Wu Ye.

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Zhu, BH., Zheng, YX., Kang, W. et al. Catalytic hydrative cyclization of aldehyde-ynamides with water for synthesis of medium-sized lactams. Sci. China Chem. 64, 1985–1989 (2021). https://doi.org/10.1007/s11426-021-1069-7

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