Ir-BiphPHOX催化的不对称氢化反应合成手性5-芳基噁唑烷-2-酮  

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

作　　者：张同利 晏君 何敬立 寇学振 申杰峰[1] 刘德龙[1] 张万斌[1,2] Zhang Tongli;Yan Jun;He Jingli;Kou Xuezhen;Shen Jiefeng;Liu Delong;Zhang Wanbin(Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs,School of Pharmacy,Shanghai Jiao Tong University,Shanghai 200240;Frontiers Science Center for Transformative Molecules,School of Chemistry and Chemical Engineering,Shanghai Jiao Tong University,Shanghai 200240)

机构地区：[1]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 [2]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

出　　处：《有机化学》2022年第6期1747-1758,共12页Chinese Journal of Organic Chemistry

基　　金：国家自然科学基金(Nos.21672142,21971162,21831005,21620102003);上海市“超级博士后”激励计划(No.2020230);中国博士后科学基金(No.2020M681276)资助项目.

摘　　要：利用轴手性Ir-BiphPHOX催化剂,首次实现了5-芳基噁唑-2-酮的不对称催化氢化反应,高收率、高选择性地合成了一系列手性5-芳基噁唑烷-2-酮类化合物.该反应对多种官能团具有良好的相容性,所得产物经简单转化可得到多种手性氨基醇类化合物或可衍生出具有生物活性的手性杂环化合物.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.

关 键 词：BiphPHOX 不对称氢化 5-芳基噁唑烷-2-酮 手性 Ir-催化氢化 

分 类 号：O626[理学—有机化学] TQ460.1[理学—化学]