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

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

研究论文

不对称合成手性3,5-二取代脯氨酸及其衍生物

  • 赵亮 ,
  • 周圣斌 ,
  • 童军华 ,
  • 王江 ,
  • 柳红
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  • 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

  网络出版日期: 2018-02-28

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.

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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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摘要

选用甘氨酸等当体镍螯合物与α，β-不饱和酮进行不对称Michael加成反应，在室温条件下，以1，8-二氮杂二环十一碳-7-烯（DBU）为碱，甲醇为溶剂，不对称合成了3，5-二取代脯氨酸及其衍生物.该方法具有操作简单、收率高、底物适用范围广的特点，为3，5-二取代脯氨酸及其衍生物的不对称合成提供了新的研究思路.

关键词： 3,5-二取代脯氨酸; 甘氨酸等当体镍螯合物; 不对称Michael加成反应

本文引用格式

赵亮 , 周圣斌 , 童军华 , 王江 , 柳红 . 不对称合成手性3,5-二取代脯氨酸及其衍生物[J]. 有机化学, 2018 , 38(6) : 1437 -1446 . DOI: 10.6023/cjoc201712005

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

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