Chin. J. Org. Chem. ›› 2013, Vol. 33 ›› Issue (09): 1932-1938.DOI: 10.6023/cjoc201305051 Previous Articles     Next Articles

Articles

D-(R)-酪氨酸的不对称催化氢化合成及其在药物合成中的应用

余坤矫a, 张振锋a, 霍小红a, 王兴广b, 刘德龙a, 张万斌a,b   

  1. a 上海交通大学药学院 上海 200240;
    b 上海交通大学化学化工学院 上海 200240
  • 收稿日期:2013-05-30 修回日期:2013-06-07 出版日期:2013-09-28 发布日期:2013-06-21
  • 通讯作者: 张振锋,张万斌 E-mail:wanbin@sjtu.edu.cn
  • 基金资助:

    上海市经济与信息化委员会基金(No. 12CH-02)资助项目

Synthesis of D-(R)-Tyrosine by Catalytic Asymmetric Hydrogenation and Its Practical Application

Yu Kunjiaoa, Zhang Zhenfenga, Huo Xiaohonga, Wang Xingguangb, Liu Delonga, Zhang Wanbina,b   

  1. a School of Pharmacy, Shanghai Jiao Tong University, Shanghai 200240;
    b School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240
  • Received:2013-05-30 Revised:2013-06-07 Online:2013-09-28 Published:2013-06-21
  • Supported by:

    Project supported by the Foundation of Shanghai Municipal Commission of Economy and Informatization (No. 12CH-02)

Using a recently developed catalyst[Rh((R,R)-QuinoxP*)(cod)]SbF6, several derivatives of D-(R)-tyrosine were prepared with up to 99% ee via catalytic asymmetric hydrogenation. The substrates chosen for asymmetric hydrogenation were readily synthesized from the inexpensive and accessible compound 4-hydroxybenzaldehyde. The product resulting from the asymmetric hydrogenation was practically applied to the preparation of an important bioactive compound sodium (R)-3-(3,4-dihydroxyphenyl)-2-hydroxypropanoate through a feasible process.

Key words: catalytic asymmetric hydrogenation, D-(R)-tyrosine, rhodium, biphosphine ligand, sodium (R)-3-(3,4-dihydr- oxyphenyl)-2-hydroxypropanoate