Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (6): 1398-1406.DOI: 10.6023/cjoc201701020 Previous Articles     Next Articles

Articles

手性辅基诱导β-脱氢氨基酸酯的非均相不对称氢化(英文)

王群a, 江黎黎a, 卢斌a, 胡北a, 谢小敏a,b, 李泽标b, 张兆国a   

  1. a. 上海交通大学化学化工学院 上海 200240;
    b. 南通常佑制药有限公司 南通 226400
  • 收稿日期:2017-01-09 修回日期:2017-02-28 发布日期:2017-03-03
  • 通讯作者: 张兆国 E-mail:zhaoguo@sjtu.edu.cn
  • 基金资助:

    国家自然科学基金(No.21472124)资助项目.

Pt/Al2O3 Catalyzed Diastereoselective Hydrogenation of β-Dehydro-amino Esters Induced by a Chiral Prosthetic Group

Wang Quna, Jiang Lilia, Lu Bina, Hu Beia, Xie Xiaomina,b, Li Zebiaob, Zhang Zhaoguoa   

  1. a. School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240;
    b. Nantong Changyou Pharmaceutical Company, Nantong 226400
  • Received:2017-01-09 Revised:2017-02-28 Published:2017-03-03
  • Contact: 10.6023/cjoc201701020 E-mail:zhaoguo@sjtu.edu.cn
  • Supported by:

    Project supported by the National Natural Sciences Foundation of China (No. 21472124).

A chiral prosthetic group induced heterogeneous diastereoselective asymmetric hydrogenation of β-dehydroamino esters, catalyzed by Pt/Al2O3, has been developed. A series of β-dehydroamino esters were successfully hydrogenated in high yields with good diastereoselectivities (dr up to 5.2:94.8). This method provides a convenient and efficient synthetic way for the preparation of chiral β-amino acid derivatives, which are key intermediates for bioactive compounds and pharmaceuticals.

Key words: sitagliptin, diastereoselectivities, β-dehydroamino esters, Pt/Al2O3, heterogeneous hydrogenation