Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (6): 1747-1758.DOI: 10.6023/cjoc202112040 Previous Articles     Next Articles

ARTICLES

Ir-BiphPHOX催化的不对称氢化反应合成手性5-芳基噁唑烷-2-酮

张同利a, 晏君b, 何敬立a, 寇学振b, 申杰峰a, 刘德龙a,*(), 张万斌a,b,*()   

  1. a 上海交通大学药学院 上海市手性药物分子工程重点实验室 上海 200240
    b 上海交通大学化学化工学院 教育部变革性分子前沿科学中心 上海 200240
  • 收稿日期:2021-12-29 修回日期:2022-02-21 发布日期:2022-03-03
  • 通讯作者: 刘德龙, 张万斌
  • 基金资助:
    国家自然科学基金(21672142); 国家自然科学基金(21971162); 国家自然科学基金(21831005); 国家自然科学基金(21620102003); 上海市“超级博士后”激励计划(2020230); 中国博士后科学基金(2020M681276)

Synthesis of Chiral 5-Aryl-2-oxazolidinones via an Ir-BiphPHOX Catalyzed Enantioselective Hydrogenation

Tongli Zhanga, Jun Yanb, Jingli Hea, Xuezhen Koub, Jiefeng Shena, Delong Liua(), Wanbin Zhanga,b()   

  1. a Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Pharmacy, Shanghai Jiao Tong University, Shanghai 200240
    b Frontiers Science Center for Transformative Molecules, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240
  • Received:2021-12-29 Revised:2022-02-21 Published:2022-03-03
  • Contact: Delong Liu, Wanbin Zhang
  • Supported by:
    National Natural Science Foundation of China(21672142); National Natural Science Foundation of China(21971162); National Natural Science Foundation of China(21831005); National Natural Science Foundation of China(21620102003); Shanghai Post-Doctoral Excellence Program(2020230); China Postdoctoral Science Foundation(2020M681276)

The enantioselective catalytic hydrogenation of 5-aryl-2-oxazolones has been achieved for the first time using the axially chiral Ir-BiphPHOX catalyst, providing the corresponding chiral 5-aryl-2-oxazolidinones in high yields and with excellent enantioselectivities. The protocol has good compatibility with a variety of functional groups, and the resulting products can be converted into various chiral amino alcohol compounds or can be transformed into a series of chiral heterocyclic compounds with various biological activities.

Key words: BiphPHOX, enantioselective hydrogenation, 5-aryl-2-oxazolidinone, chirality, Ir-catalyzed hydrogenation