Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (6): 1437-1446.DOI: 10.6023/cjoc201712005 Previous Articles     Next Articles

Articles

不对称合成手性3,5-二取代脯氨酸及其衍生物

赵亮a,b,c, 周圣斌a,b, 童军华a,b,c, 王江a,b, 柳红a,b   

  1. a 中国科学院上海药物研究所 新药研究国家重点实验室和受体结构与功能重点实验室 上海 201203;
    b 中国科学院大学 北京 100049;
    c 中国科学技术大学苏州纳米学院 苏州 215123
  • 收稿日期:2017-12-04 修回日期:2018-02-12 出版日期:2018-06-25 发布日期:2018-02-28
  • 通讯作者: 王江,E-mail:hliu@simm.ac.cn;柳红,E-mail:jwang@simm.ac.cn E-mail:hliu@simm.ac.cn;jwang@simm.ac.cn
  • 基金资助:

    国家自然科学基金(Nos.81620108027,21632008,21672231,21472209)、国家重大科学计划(No.2015CB910304)和上海市科委课题(No.15QA1404400)资助项目.

Asymmetric Synthesis of 3, 5-Disubstituted Prolines

Zhao Lianga,b,c, Zhou Shengbina,b, Tong Junhuaa,b,c, Wang Jianga,b, Liu Honga,b   

  1. 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:2017-12-04 Revised:2018-02-12 Online:2018-06-25 Published:2018-02-28
  • Contact: 10.6023/cjoc201712005 E-mail:hliu@simm.ac.cn;jwang@simm.ac.cn
  • 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).

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