有机化学 ›› 2019, Vol. 39 ›› Issue (8): 2188-2195.DOI: 10.6023/cjoc201904079 上一篇    下一篇

所属专题: 陈茹玉先生诞辰100周年

研究论文

基于手性氨硼烷的β-烯胺腈不对称转移氢化反应

周启文a, 冯向青b, 杨晶a, 杜海峰b   

  1. a 北京化工大学生命科学与技术学院 化工资源有效利用国家重点实验室 北京 100029;
    b 中国科学院化学研究所北京国家分子科学研究中心 中国科学院分子识别与功能重点实验室 北京 100190
  • 收稿日期:2019-04-30 修回日期:2019-06-06 出版日期:2019-08-25 发布日期:2019-06-12
  • 通讯作者: 杨晶, 杜海峰 E-mail:yangji@mail.buct.edu.cn;haifengdu@iccas.ac.cn
  • 基金资助:

    国家自然科学基金(Nos.21825108,91856103)资助项目.

Asymmetric Transfer Hydrogenations of β-Enamine Cyanide with Chiral Ammonia Borane

Zhou Qiwena, Feng Xiangqingb, Yang Jinga, Du Haifengb   

  1. a Key Laboratory of Chemical Resource Engineering Beijing Key Laboratory of Bioprocess, College of Life Sciences and Technology, Beijing University of Chemical Technology, Beijing 100029;
    b Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190
  • Received:2019-04-30 Revised:2019-06-06 Online:2019-08-25 Published:2019-06-12
  • Contact: 10.6023/cjoc201904079 E-mail:yangji@mail.buct.edu.cn;haifengdu@iccas.ac.cn
  • Supported by:

    Project supported by the National Natural Science Foundation of China (Nos. 21825108, 91856103).

不对称转移氢化是获得光学活性化合物的一类重要反应.利用手性磷酸和氨硼烷释放氢气原位生成手性氨硼烷,水作为添加剂促进手性氨硼烷的循环再生,顺利实现了β-烯胺腈的不对称转移氢化反应,以48%~98%的收率和61%~95% ee获得了一系列手性β-胺基腈类化合物.

关键词: 不对称转移氢化, 手性氨硼烷, 手性磷酸, 氨硼烷, β-烯胺腈

The asymmetric transfer hydrogenation represents one important class of reactions for the synthesis of optically active compounds. A chiral ammonia borane was generated in situ from an H2 release reaction between chiral phosphoric acid and ammonia borane, which could be regenerated by the assistance of water after the hydrogen transfer process and made this reaction catalytic. With this chiral ammonia borane, asymmetric transfer hydrogenations of β-enamine cyanides were realized to afford the desired products in 48%~98% yields with 61%~95% ee.

Key words: asymmetric transfer hydrogenation, chiral ammonia borane, chiral phosphoric acid, ammonia borane, β-enamino cyanide