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l-Valine Dipeptide Organocatalysts with Two Amide Units for the Direct Asymmetric Aldol Reaction in Brine

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Abstract

A series of valine dipeptide organocatalysts containing a primary amine group and two amide units have been developed and evaluated in the direct asymmetric intermolecular aldol reaction of 4-nitrobenzaldehyde and cyclohexanone. When 2,4-dinitrophenol (DNP) was used as an acidic additive, the catalyzed reactions of various aldehydes and ketones gave the corresponding aldol products with moderate to high enantioselectivities (up to 95%) and diastereoselectivities (up to >99/1, anti/syn) in the presence of 3c in brine.

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Acknowledgements

We are grateful for the financial support from the National Natural Science Foundation of China (no. 20802025) and the Jilin Provincial Science &Technology Sustentation Program (no. 20090585, 20100538).

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Authors and Affiliations

  1. College of Chemistry, Jilin University, Changchun, 130012, People’s Republic of China

    Wenbo Huang, Hua Tian, Hao Xu, Qingwen Liu & Suoqin Zhang

  2. Key Laboratory for Molecular Enzymology and Engineering of Ministry of Education, Jilin University, Changchun, 130012, People’s Republic of China

    Liangyu Zheng

Authors
  1. Wenbo Huang
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  2. Hua Tian
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  3. Hao Xu
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  4. Liangyu Zheng
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  5. Qingwen Liu
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  6. Suoqin Zhang
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Corresponding authors

Correspondence to Liangyu Zheng or Suoqin Zhang.

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Huang, W., Tian, H., Xu, H. et al. l-Valine Dipeptide Organocatalysts with Two Amide Units for the Direct Asymmetric Aldol Reaction in Brine. Catal Lett 141, 872–876 (2011). https://doi.org/10.1007/s10562-011-0589-z

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  • DOI: https://doi.org/10.1007/s10562-011-0589-z

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