有机化学 ›› 2019, Vol. 39 ›› Issue (8): 2119-2130.DOI: 10.6023/cjoc201904060 上一篇    下一篇

所属专题: 陈茹玉先生诞辰100周年

综述与进展

金属化亚甲胺叶立德在手性非天然α-氨基酸合成中的应用研究进展

卫亮a, 肖露a, 胡远征a, 汪昨非a, 陶海燕a, 王春江a,b   

  1. a 武汉大学化学与分子科学学院 有机硅化合物及材料教育部工程研究中心 武汉 430072;
    b 南开大学 元素有机化学国家重点实验室 天津 300071
  • 收稿日期:2019-04-24 修回日期:2019-05-25 出版日期:2019-08-25 发布日期:2019-06-03
  • 通讯作者: 王春江 E-mail:cjwang@whu.edu.cn
  • 基金资助:

    国家自然科学基金(Nos.21525207,21772147)和中国博士后科研基金(No.2017M620331)资助项目.

Recent Advances in Metallated Azomethine Ylides for the Synthesis of Chiral Unnatural α-Amino Acids

Wei Lianga, Xiao Lua, Hu Yuanzhenga, Wang Zuofeia, Tao Haiyana, Wang Chunjianga,b   

  1. a Engineering Research Center of Organosilicon Compounds & Materials, Ministry of Education, College of Chemistry and Molecular Sciences, Wuhan University, Wuhan 430072;
    b State Key Laboratory of Elemento-organic Chemistry, Nankai University, Tianjin 300071
  • Received:2019-04-24 Revised:2019-05-25 Online:2019-08-25 Published:2019-06-03
  • Contact: 10.6023/cjoc201904060 E-mail:cjwang@whu.edu.cn
  • Supported by:

    Project supported by the National Natural Science Foundation of China (Nos. 21525207, 21772147) and the China Postdoctoral Science Foundation (No. 2017M620331).

非天然α-氨基酸作为一类在合成与药物化学领域都有着广泛应用的化合物,发展其高效的合成方法一直以来都是有机化学界的研究热点.其中由原料来源丰富、价廉易得的亚胺酯原位制备的金属化亚甲胺叶立德,作为亲核试剂参与的不对称α-官能团化反应,已经成为构建非天然氨基酸衍生物的重要手段.在过去近20年中,金属路易斯酸催化的基于亚甲胺叶立德合成非天然氨基酸的报道不断涌现.根据亲电试剂种类划分,总结了近年来金属化亚甲胺叶立德在非天然氨基酸合成中的研究进展.

关键词: 亚甲胺叶立德, 不对称催化, 非天然α-氨基酸

The development of efficient methods for the preparation of unnatural amino acids has long been an important goal since their widely application in synthetic and medicinal chemistry. The asymmetric α-functionalization of nucleophilic metalated azomethine ylides, which could be in situ-generated from readily-available aldimine esters, has been recogonized as a powerful strategy to synthesize unnatural amino acids. Over the past 20 years, tranistion metal-catalyzed asymmetric construction of unnatural amino acids using azomethine ylides have been extensively studied. In this review, the progress on metallated azomethine ylides invovled aymmetric transformation for the synthesis of unnatural amino acids is summarized according to eletrophilic reagents.

Key words: azomethine ylide, asymmetric catalysis, unnatural α-amino acid