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Chinese Journal of Organic Chemistry >

2018 , Vol. 38 >Issue 6: 1437 - 1446

DOI: https://doi.org/10.6023/cjoc201712005

Articles

Asymmetric Synthesis of 3, 5-Disubstituted Prolines

  • Zhao Liang ,
  • Zhou Shengbin ,
  • Tong Junhua ,
  • Wang Jiang ,
  • Liu Hong
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  • a State Key Laboratory of Drug Research and CAS Key Laboratory of Receptor Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203;
    b University of Chinese Academy of Sciences, Beijing 100049;
    c Nano Science and Technology Institute, University of Science and Technology of China, Suzhou 215123

Received date: 2017-12-04

  Revised date: 2018-02-12

  Online published: 2018-02-28

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 81620108027, 21632008, 21672231, 21472209), the Major Project of Chinese National Programs for Fundamental Research and Development (No. 2015CB910304) and the Shanghai Science and Technology Development Fund (No. 15QA1404400).

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Abstract

Highly diastereoselective Michael addition reactions of chiral Ni(Ⅱ)-complex of glycine with α,β-unsaturated ketones in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) and MeOH at ambient temperature were achieved. The operationally convenient procedure for preparation of the target products renders that this method is an attractive strategy for practical synthesis of 3,5-disubstituted prolines.

Key words： 3,5-disubstituted proline; Ni (II)-complex of glycine; asymmetric Michael addition

Cite this article

Zhao Liang , Zhou Shengbin , Tong Junhua , Wang Jiang , Liu Hong . Asymmetric Synthesis of 3, 5-Disubstituted Prolines[J]. Chinese Journal of Organic Chemistry, 2018 , 38(6) : 1437 -1446 . DOI: 10.6023/cjoc201712005

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