Chiral Polymeric Diamine Ligands for Iridium-Catalyzed Asymmetric Transfer Hydrogenation

被引:9
作者
Lin, Yaodong [1 ]
Xu, Guangqing [1 ]
Tang, Wenjun [1 ,2 ]
机构
[1] Univ Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Chem Biol, Shanghai 200032, Peoples R China
[2] Univ Chinese Acad Sci, Hangzhou Inst Adv Study, Sch Chem & Mat Sci, Hangzhou 310024, Peoples R China
基金
国家重点研发计划;
关键词
DEPENDENT TRANSFER HYDROGENATION; SOLUBLE CARBONYL-COMPOUNDS; ALPHA-KETO ACIDS; CP-ASTERISK; REDUCTIVE AMINATION; COMPLEX; HYDRIDE;
D O I
10.1021/jacs.4c09516
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A series of polymeric chiral diamine ligands are developed by diboron-templated asymmetric reductive couplings, and their iridium complexes Ir-polydiamines are efficient and recyclable catalysts for asymmetric transfer hydrogenation (ATH) of functionalized ketones, affording a series of optically active secondary alcohols in excellent enantioselectivities (up to 99% ee) and unprecedentedly high total TONs (12,000, six cycles). Ir-polydiamine catalysts with longer chains offered higher reactivities, providing a plausible deactivation mechanism and practical solutions of ATH for vitamin B5 and phenylephrine.
引用
收藏
页码:27736 / 27744
页数:9
相关论文
共 43 条
[1]   Isolation and crystal structure of a water-soluble iridium hydride: A robust and highly active catalyst for acid-catalyzed transfer hydrogenations of carbonyl compounds in acidic media [J].
Abura, T ;
Ogo, S ;
Watanabe, Y ;
Fukuzumi, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (14) :4149-4154
[2]   STUDIES ON THE CATALYTIC ASYMMETRIC-SYNTHESIS OF OPTICALLY-ACTIVE MEDICINES [J].
ACHIWA, K .
YAKUGAKU ZASSHI-JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAPAN, 1995, 115 (09) :681-699
[3]   Using Soluble Polymer Supports To Facilitate Homogeneous Catalysis [J].
Bergbreiter, David E. ;
Tian, Jianhua ;
Hongfa, Chayanant .
CHEMICAL REVIEWS, 2009, 109 (02) :530-582
[4]   Practical and Asymmetric Reductive Coupling of Isoquinolines Templated by Chiral Diborons [J].
Chen, Dongping ;
Xu, Guangqing ;
Zhou, Qinghai ;
Chung, Lung Wa ;
Tang, Wenjun .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (29) :9767-9770
[5]  
[窦骁勇 Dou Xiaoyong], 2020, [中国医药工业杂志, Chinese Journal of Pharmaceuticals], V51, P145
[6]   Ruthenium(II)-catalyzed asymmetric transfer hydrogenation of ketones using a formic acid-triethylamine mixture [J].
Fujii, A ;
Hashiguchi, S ;
Uematsu, N ;
Ikariya, T ;
Noyori, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (10) :2521-2522
[7]   Asymmetric transfer hydrogenation: chiral ligands and applications [J].
Gladiali, S ;
Alberico, E .
CHEMICAL SOCIETY REVIEWS, 2006, 35 (03) :226-236
[8]   Iridium/f-ampha-catalyzed asymmetric hydrogenation of aromatic α-keto esters [J].
Gu, Guoxian ;
Yang, Tilong ;
Lu, Jiaxiang ;
Wen, Jialin ;
Dang, Li ;
Zhang, Xumu .
ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (07) :1209-1212
[9]   Exploring Heteroaromatic Rings as a Replacement for the Labile Amide of Antiplasmodial Pantothenamides [J].
Guan, Jinming ;
Spry, Christina ;
Tjhin, Erick T. ;
Yang, Penghui ;
Kittikool, Tanakorn ;
Howieson, Vanessa M. ;
Ling, Harriet ;
Starrs, Lora ;
Duncan, Dustin ;
Burgio, Gaetan ;
Saliba, Kevin J. ;
Auclair, Karine .
JOURNAL OF MEDICINAL CHEMISTRY, 2021, 64 (08) :4478-4497
[10]   The Synthesis of Chiral α-Aryl α-Hydroxy Carboxylic Acids via RuPHOX-Ru Catalyzed Asymmetric Hydrogenation [J].
Guo, Huan ;
Li, Jing ;
Liu, Delong ;
Zhang, Wanbin .
ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (20) :3665-3673