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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CCDC 2084987 (2i) and 1811930 (4a) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Date Centre
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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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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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DOI: https://doi.org/10.1007/s11426-021-1069-7