Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (2): 376-383.DOI: 10.6023/cjoc201907053 Previous Articles     Next Articles

通过不对称氢转移/动态动力学拆分合成碳环N3-嘌呤核苷

张齐英, 张一铭, 郝二军, 白娟, 渠桂荣, 郭海明   

  1. 河南师范大学化学化工学院 绿色化学介质与反应教育部重点实验室 精细化学品绿色制造河南省协同创新中心 河南省有机功能分子与药物创新重点实验室 河南新乡 453007
  • 收稿日期:2019-07-30 修回日期:2019-09-30 出版日期:2020-02-25 发布日期:2019-10-25
  • 通讯作者: 郭海明 E-mail:ghm@htu.edu.cn
  • 基金资助:
    国家自然科学基金(Nos.21602045,U1604283)和高等学校学科创新引智计划(111计划,No.D17007)资助项目.

Asymmetric Transfer Hydrogenation via Dynamic Kinetic Resolution for the Construction of Carbocyclic N3-Purine Nucleosides

Zhang Qiying, Zhang Yiming, Hao Erjun, Bai Juan, Qu Guirong, Guo Haiming   

  1. Henan Key Laboratory of Organic Functional Molecules and Drug Innovation, Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007
  • Received:2019-07-30 Revised:2019-09-30 Online:2020-02-25 Published:2019-10-25
  • Supported by:
    Project supported by the National Natural Science Foundation of China (Nos. 21602045, U1604283), and the Overseas Expertise Introduction Project for Discipline Innovation (111 Project, No. D17007).

N3-Purine nucleoside can be employed as a potent dual inhibitor to inhibit viruses more effectively because it could be possibly recognized by both purine-and pyrimidine-metabolizing enzymes. Herein, an asymmetric transfer hydrogenation via dynamic kinetic resolution of rac-α-(purin-3-yl)cyclopentones has been developed to produce a wide range of carbocyclic N3-purine nucleosides in high yields and excellent stereoselectivities. Moreover, the catalytic system was suitable for rac-α-pyrimidinyl cyclopentones. With additional transformations, several 2'-F-, AcS-, N3-modified carbocyclic nucleosides could be obtained with good to excellent yields and excellent enantioselectivities.

Key words: carbocyclic nucleosides, dual inhibitors, dynamic kinetic resolution, asymmetric transfer hydrogenation