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Phosphine-catalyzed [4+2] annulations of α-aminonitriles with allenoates: Synthesis of functionalized tetrahydropyridines

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Abstract

Phosphine-catalyzed [4+2] annulations of 2-(acetoxymethyl)buta-2,3-dienoates with α-aminonitriles have been developed, in which α-aminonitriles serve as C, N-bisnucleophilic reaction partners and 2-(acetoxymethyl)buta-2,3-dienoates as “C4 synthons” respectively. A number of α-aminonitriles could be successfully applied to giving multifunctional desired products using PPh3 as catalyst. This method provides a facile entry to access polysubstituted tetrahydropyridines bearing quaternary carbon centers. The possible reaction mechanism was also proposed.

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Authors and Affiliations

  1. Department of Organic Chemistry, College of Chemistry, Jilin University, Changchun, 130012, P. R. China

    Hochol Jang, Wei Liu, Xiao’an Zhang Sean & Weiwei Liao

  2. Department of Chemistry, Kim Il Sung University, Pyongyang, D. P. R. Korea

    Hochol Jang

Authors
  1. Hochol Jang
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  2. Wei Liu
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  3. Xiao’an Zhang Sean
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  4. Weiwei Liao
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Corresponding authors

Correspondence to Xiao’an Zhang Sean or Weiwei Liao.

Additional information

Supported by the National Natural Science Foundation of China(No. 21372096).

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Jang, H., Liu, W., Zhang Sean, X. et al. Phosphine-catalyzed [4+2] annulations of α-aminonitriles with allenoates: Synthesis of functionalized tetrahydropyridines. Chem. Res. Chin. Univ. 32, 385–389 (2016). https://doi.org/10.1007/s40242-016-5495-x

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  • DOI: https://doi.org/10.1007/s40242-016-5495-x

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