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Regioselective synthesis of functionalized dihydroquinolines via organocatalytic allylic alkylation

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Abstract

The regioselective allylic alkylation of 1,2-dihydroquinolines and Morita-Baylis-Hillman(MBH) adducts has been developed. By surveying various reaction parameters, we summarize the effects of temperatures, relative reactant doses, catalysts, solvents and N-protected groups on the regioselectivity of this transformation. This method provides a facile protocol for the preparation of allylic α-substituted dihydroquinolines.

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Authors and Affiliations

  1. Department of Pharmacology, School of Pharmaceutical Science, Jilin University, Changchun, 130012, P. R. China

    Xiaoyuan Ma & Yi Wu

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

    Yanjing Zhang & Weiwei Liao

  3. College of Life Sciences, Jilin University, Changchun, 130012, P. R. China

    Lesheng Teng & Jing Xie

Authors
  1. Xiaoyuan Ma
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  2. Yi Wu
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  3. Yanjing Zhang
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  4. Lesheng Teng
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  5. Jing Xie
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  6. Weiwei Liao
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Corresponding authors

Correspondence to Jing Xie or Weiwei Liao.

Additional information

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

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Ma, X., Wu, Y., Zhang, Y. et al. Regioselective synthesis of functionalized dihydroquinolines via organocatalytic allylic alkylation. Chem. Res. Chin. Univ. 32, 634–640 (2016). https://doi.org/10.1007/s40242-016-5481-3

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  • DOI: https://doi.org/10.1007/s40242-016-5481-3

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