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One-pot synthesis of polysubstituted 2-piperidinones from aromatic aldehydes, nitromethane, ammonium acetate, and dialkyl malonates

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Abstract

A pseudo-five-component reaction for one-pot synthesis of polysubstituted 2-piperidinones from two equivalent aromatic aldehydes, nitromethane, ammonium acetate, and dialkyl malonates is reported. Interestingly, the formation of products was highly stereoselective. Two different stereochemical classes of polysubstituted 2-piperidinones were provided depending on the substituent position of the aromatic aldehydes.

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Acknowledgments

Financial support of this research by the National Natural Science Foundation of China (NNSFC 21173181) is gratefully acknowledged by the authors. This project was funded by the Priority Academic Program Development of Jiangsu Higher Education Institutions.

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Authors and Affiliations

  1. School of Chemistry and Chemical Engineering, Yangzhou University, 180 Siwangting Street, Yangzhou, People’s Republic of China

    Hui Liu, Qian Sun, Zhengquan Zhou, Juanjuan Liu, Jing Yang & Cunde Wang

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  1. Hui Liu
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  2. Qian Sun
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  3. Zhengquan Zhou
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  4. Juanjuan Liu
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  5. Jing Yang
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  6. Cunde Wang
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Corresponding author

Correspondence to Cunde Wang.

Electronic supplementary material

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706_2012_912_MOESM1_ESM.pdf

Supplementary Material Full characterization data and copies of the 1H and 13C NMR spectra of all compounds as well as crystallographic data for 4a, 4c, and 4y can be found in the Supplementary Material available online. (PDF 4913 kb)

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Liu, H., Sun, Q., Zhou, Z. et al. One-pot synthesis of polysubstituted 2-piperidinones from aromatic aldehydes, nitromethane, ammonium acetate, and dialkyl malonates. Monatsh Chem 144, 1031–1041 (2013). https://doi.org/10.1007/s00706-012-0912-4

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  • DOI: https://doi.org/10.1007/s00706-012-0912-4

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