Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (8): 2188-2195.DOI: 10.6023/cjoc201904079 Previous Articles     Next Articles

Special Issue: 陈茹玉先生诞辰100周年

Articles

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).

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