Ru-catalyzed asymmetric transfer hydrogenation of racemic /3-keto γ-lactams via dynamic kinetic resolution

被引：0
|
作者：
Malekar, Pushpa, V [1 ,2 ]
More, Ganesh, V [1 ]
Ramana, Chepuri, V [1 ,2 ]
机构：
[1] CSIR Natl Chem Lab, Div Organ Chem, Dr Homi Bhabha Rd, Pune 411008, India
[2] Acad Sci & Innovat Res AcSIR, Ghaziabad 201002, India
来源：
TETRAHEDRON | 2024年 / 167卷
关键词：
Dynamic kinetic resolution; Asymmetric transfer hydrogenation; Fluroquinolone antibiotics; /3-keto gamma-lactams; (R)-1-((R)-Pyrrolidin-3-yl)ethan-1-ol; SYN-1,2-DIOL DERIVATIVES; RESISTANCE; SEROTONIN; DRUGS;
D O I：
10.1016/j.tet.2024.134293
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The enantioselective transfer hydrogenation of racemic /3-keto gamma-lactams via dynamic kinetic resolution using a chiral Ru(II) catalyst has been developed for the synthesis of optically active /3-hydroxyl lactams with excellent conversion (up to 99 %), high diastereomeric ratio (dr dr 93:07) and enantiomeric selectivity (89 % ee ). The reaction proceeded by using HCO2H/Et3N 2 H/Et 3 N as hydrogen donor and features mild, additive free reaction conditions, fast crystallization, broad substrate scope, and an operationally simpler setup than that for molecular hydrogenation.
引用
收藏
页数：8
相关论文
共 50 条
  • [41] Transformation of Alkynes into Chiral Alcohols via TfOH-Catalyzed Hydration and Ru-Catalyzed Tandem Asymmetric Hydrogenation
    Liu, Sensheng
    Liu, Huan
    Zhou, Haifeng
    Liu, Qixing
    Lv, Jinliang
    ORGANIC LETTERS, 2018, 20 (04) : 1110 - 1113
  • [42] Efficient and Scalable Kinetic Resolution of Racemic 4-Formyl-[2.2]paracyclophane via Asymmetric Transfer Hydrogenation
    Delcourt, Marie-Leonie
    Turcaud, Serge
    Benedetti, Erica
    Micouin, Laurent
    ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (08) : 1213 - 1218
  • [43] Dynamic kinetic resolution via asymmetric ketone hydrogenation.
    Shultz, CS
    Chen, CY
    Krska, S
    Sun, YK
    Rosner, T
    Howley, M
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2003, 226 : U96 - U96
  • [44] Chiral 1,2,3,4-tetrahydroquinolinyl-oxazoline ligands for Ru-catalyzed asymmetric transfer hydrogenation of ketones
    Zhou, YB
    Tang, FY
    Xu, HD
    Wu, XY
    Ma, JA
    Zhou, QL
    TETRAHEDRON-ASYMMETRY, 2002, 13 (05) : 469 - 473
  • [45] Kinetic resolution of racemic secondary alcohols by Ru-II-catalyzed hydrogen transfer
    Hashiguchi, S
    Fujii, A
    Haack, KJ
    Matsumura, K
    Ikariya, T
    Noyori, R
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1997, 36 (03) : 288 - 290
  • [46] Asymmetric Transfer Hydrogenation via Dynamic Kinetic Resolution for the Construction of Carbocyclic N3-Purine Nucleosides
    Zhang, Qiying
    Zhang, Yiming
    Hao, Erjun
    Bai, Juan
    Qu, Guirong
    Guo, Haiming
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2020, 40 (02) : 376 - 383
  • [47] New efficient P,N,O-tridentate ligands for Ru-catalyzed asymmetric transfer hydrogenation
    Dai, HC
    Hu, XP
    Chen, HL
    Bai, CM
    Zheng, Z
    TETRAHEDRON-ASYMMETRY, 2003, 14 (11) : 1467 - 1472
  • [48] Enantioselective Synthesis of 1-Aryl-Substituted Tetrahydroisoquinolines Through Ru-Catalyzed Asymmetric Transfer Hydrogenation
    Perez, Marc
    Wu, Zi
    Scalone, Michelangelo
    Ayad, Tahar
    Ratovelomanana-Vidal, Virginie
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (29) : 6503 - 6514
  • [49] Highly Efficient Kinetic Resolution of Aryl-Alkenyl Alcohols by Ru-Catalyzed Hydrogen Transfer
    You, Yipeng
    Jin, Ming Yu
    Tao, Guanyu
    Xing, Xiangyou
    MOLECULES, 2021, 26 (24):
  • [50] Synthesis of Enantiopure γ-Lactones via a RuPHOX-Ru Catalyzed Asymmetric Hydrogenation of γ-Keto Acids
    Li, Jing
    Ma, Yujie
    Lu, Yufei
    Liu, Yangang
    Liu, Delong
    Zhang, Wanbin
    ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (05) : 1146 - 1153
12345