Dynamic kinetic resolution of an azlactone catalyzed by octahedral chiral-at-metal cobalt(iii) complexes under phase-transfer alcoholysis

被引:0
|
作者
Emelyanov, Mikhail A. [1 ]
Rozhkov, Evgeniy, V [1 ,2 ]
Maleev, Victor I. [1 ]
Larionov, Vladimir A. [1 ]
机构
[1] Russian Acad Sci, AN Nesmeyanov Inst Organoelement Cpds, Moscow 119334, Russia
[2] DI Mendeleev Univ Chem Technol Russia, Russian Acad Sci, Higher Chem Coll, Moscow 125047, Russia
基金
俄罗斯科学基金会;
关键词
kinetic resolution; azlactone; amino acids; chiral-at-metal; cobalt( iii ) complexes; AMINO-ACIDS; SCHIFF-BASES;
D O I
10.1016/j.mencom.2024.02.015
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A family of well-defined octahedral cationic chiral-atcobalt( iii ) catalysts based on ( R , R )-1,2-cyclohexanediamine and ( R , R )-1,2-diphenylethylenediamine has been examined in the dynamic kinetic resolution of an azlactone derived from N -benzoyl- tert -leucine . The reactions catalyzed by 10 mol% of Co iii complexes in the presence of 1 M aqueous NaOH solution under phase-transfer alcoholysis afforded the corresponding benzyl ester of tert -leucine with up to 76% yield and up to 66% enantioselectivity ( ee ).
引用
收藏
页码:206 / 208
页数:3
相关论文
共 50 条
  • [1] Origin of Enantioselectivity in Chiral Phosphoric-Acid-Catalyzed Azlactone Dynamic Kinetic Resolution
    De Castro, Pedro P.
    Batista, Gabriel M. F.
    Amarante, Giovanni W.
    Dos Santos, Helio F.
    JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (18): : 13169 - 13174
  • [2] Dynamic Kinetic Resolution of Azlactones via Phase-Transfer
    Wakafuji, Kodai
    Iwasa, Satsuki
    Ouchida, Kina N.
    Cho, Hyemin
    Dohi, Hirotsugu
    Yamamoto, Eiji
    Kamachi, Takashi
    Tokunaga, Makoto
    ACS CATALYSIS, 2021, 11 (22) : 14067 - 14075
  • [3] Expanding the Family of Octahedral Chiral-at-Metal Cobalt(III) Catalysts by Introducing Tertiary Amine Moiety into the Ligand
    Savel'yeva, Tat'yana F.
    Khromova, Olga V.
    Larionov, Vladimir A.
    Smol'yakov, Alexander F.
    Fedyanin, Ivan V.
    Belokon, Yuri N.
    Maleev, Victor I.
    CATALYSTS, 2021, 11 (02) : 1 - 11
  • [4] Kinetic and Dynamic Kinetic Resolution of Racemic Tertiary Bromides by Pentanidium-Catalyzed Phase-Transfer Azidation
    Ren, Jingyun
    Ban, Xu
    Zhang, Xin
    Tan, Choon-Hong
    Lee, Richmond
    Advanced Materials, 2020, 59 (23) : 9140 - 9143
  • [5] Kinetic and Dynamic Kinetic Resolution of Racemic Tertiary Bromides by Pentanidium-Catalyzed Phase-Transfer Azidation
    Ren, Jingyun
    Ban, Xu
    Zhang, Xin
    Tan, Siu Min
    Lee, Richmond
    Tan, Choon-Hong
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (23) : 9055 - 9058
  • [6] PHASE-TRANSFER REACTIONS CATALYZED BY METAL-COMPLEXES
    ALPER, H
    ACS SYMPOSIUM SERIES, 1987, 326 : 8 - 14
  • [7] Post-Modification of Octahedral Chiral-at-Metal Cobalt(III) Complexes by Suzuki-Miyaura Cross-Coupling and Evaluation of Their Catalytic Activity
    Khromova, Olga, V
    Emelyanov, Mikhail A.
    Stoletova, Nadezhda, V
    Bodunova, Ekaterina E.
    Prima, Darya O.
    Smol'yakov, Alexander F.
    Eremenko, Igor L.
    Maleev, Victor I.
    Larionov, Vladimir A.
    ORGANOMETALLICS, 2023, 42 (18) : 2505 - 2513
  • [8] Metal complexes-catalyzed hydrolysis and alcoholysis of organic substrates and their application to kinetic resolution
    Tokunaga, Makoto
    Aoyama, Hiroshi
    Kiyosu, Junya
    Shirogane, Yuki
    Iwasawa, Tetsuo
    Obora, Yasushi
    Tsuji, Yasushi
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2007, 692 (1-3) : 472 - 480
  • [9] Chiral octahedral complexes of Co(III) as catalysts for asymmetric epoxidation of chalcones under phase transfer conditions
    Larionov, Vladimir A.
    Markelova, Elina P.
    Smol'yakov, Alexander F.
    Savel'yeva, Tat'yana F.
    Maleev, Victor I.
    Belokon, Yuri N.
    RSC ADVANCES, 2015, 5 (89): : 72764 - 72771
  • [10] Alkylative kinetic resolution of vicinal diols under phase-transfer conditions: a chiral ammonium borinate catalysis
    Pawliczek, Martin
    Hashimoto, Takuya
    Maruoka, Keiji
    CHEMICAL SCIENCE, 2018, 9 (05) : 1231 - 1235