Citation: Peng Fei YAN, Wen Bin SUN, Guang Ming LI, Chun Hong NIE, Zheng Yu YUE. Efficient C₂-Symmetric Chiral Schiff Bases for Lanthanide-catalyzed Asymmetric Hydrogenation of Acetophenone[J]. Chinese Chemical Letters, ;2006, 17(10): 1297-1300. shu

Efficient C₂-Symmetric Chiral Schiff Bases for Lanthanide-catalyzed Asymmetric Hydrogenation of Acetophenone

School of Chemistry and Materials Science, Heilongjiang University, Harbin 150080

Received Date: 7 April 2006

Fund Project: This work is financially supported by the National Natural Science Foundation of China (No. 20271018 & 20572018), Heilongjiang Province (ZJG0504, 1055HZ001 & GB04A416) and Heilongjiang University.

An array of C₂-symmetric chiral Schiff bases of substituted salicylaldehyde (1R, 2R)-1,2-cyclohexanediamine and (R)-(+)-2, 2'-diamino-1, 1'-binaphthalene, incorporated with lanthanide complexes, have been applied as catalysts for asymmetric hydrogenation of acetophenone for the first time. Highly enantioselective product with 90% enantiomeric excess (e.e.) was obtained when the catalyst, hybridized by the bulky electron-donating 3, 5-di-tert-butyl substituted Schiff base (2) and SmCl₃·4THF, was employed.
- Chiral Schiff base,
- lanthanide (Ⅲ) complexes,
- asymmetric hydrogenation,
- aceto-phenone,
- 2-propanol
1. [1]
  Xiaofen GUAN , Yating LIU , Jia LI , Yiwen HU , Haiyuan DING , Yuanjing SHI , Zhiqiang WANG , Wenmin WANG . Synthesis, crystal structure, and DNA-binding of binuclear lanthanide complexes based on a multidentate Schiff base ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2486-2496. doi: 10.11862/CJIC.20240122
2. [2]
  Yingyue ZHANG , Liuqing KANG , Yating YANG , Xiaofen GUAN , Wenmin WANG . Crystal structure and antibacterial activity of two Gd₂ complexes based on polydentate Schiff-base ligands. Chinese Journal of Inorganic Chemistry, 2025, 41(9): 1867-1877. doi: 10.11862/CJIC.20250100
3. [3]
  Ruixue Liu , Xiaobing Ding , Qiwei Lang , Gen-Qiang Chen , Xumu Zhang . Enantioselective and divergent construction of chiral amino alcohols and oxazolidin-2-ones via Ir-f-phamidol-catalyzed dynamic kinetic asymmetric hydrogenation. Chinese Chemical Letters, 2025, 36(3): 110037-. doi: 10.1016/j.cclet.2024.110037
4. [4]
  Tao Yu , Vadim A. Soloshonok , Zhekai Xiao , Hong Liu , Jiang Wang . Probing the dynamic thermodynamic resolution and biological activity of Cu(Ⅱ) and Pd(Ⅱ) complexes with Schiff base ligand derived from proline. Chinese Chemical Letters, 2024, 35(4): 108901-. doi: 10.1016/j.cclet.2023.108901
5. [5]
  Yuanyu YANG , Jianhua XUE , Yujia BAI , Lulu CUI , Dongdong YANG , Qi MA . Design, synthesis, and detection of Al³⁺ of two zinc complexes based on Schiff base ligands. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1207-1216. doi: 10.11862/CJIC.20250005
6. [6]
  Maitri Bhattacharjee , Rekha Boruah Smriti , R. N. Dutta Purkayastha , Waldemar Maniukiewicz , Shubhamoy Chowdhury , Debasish Maiti , Tamanna Akhtar . Synthesis, structural characterization, bio-activity, and density functional theory calculation on Cu(Ⅱ) complexes with hydrazone-based Schiff base ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1409-1422. doi: 10.11862/CJIC.20240007
7. [7]
  Huihua GONG , Tianhua CUI , Li JI , Jichuan ZHANG , Liyuan ZHANG , Yan CHEN , Zhenye WANG , Jiaqi XU , Ruixiang LI . Hydrogenation of CO₂ to formate catalyzed by N-heterocyclic carbene-nitrogen-phosphine chelated iridium(Ⅰ) complexes. Chinese Journal of Inorganic Chemistry, 2025, 41(12): 2609-2620. doi: 10.11862/CJIC.20250170
8. [8]
  Fozia Nazir , Syeda Sundas Musawar , Ashfaq Ahmad Khan , Bilal Akram , Farid Ahmed . Chromogenic and fluorogenic Schiff base sensors. Chinese Journal of Structural Chemistry, 2025, 44(12): 100751-100751. doi: 10.1016/j.cjsc.2025.100751
9. [9]
  You-Song Ding , Qing-Song Yang , Zhiping Zheng . Pentavalent praseodymium complexes culminated in the pursuit of high-valence lanthanide compounds. Chinese Journal of Structural Chemistry, 2025, 44(11): 100696-100696. doi: 10.1016/j.cjsc.2025.100696
10. [10]
  Zihe SONG , Jinjin ZHAO , Ning REN , Jianjun ZHANG . Crystal structure, thermal analysis, and luminescence properties of six heterocyclic lanthanide complexes. Chinese Journal of Inorganic Chemistry, 2026, 42(1): 181-192. doi: 10.11862/CJIC.20250126
11. [11]
  Ming Huang , Xiuju Cai , Yan Liu , Zhuofeng Ke . Base-controlled NHC-Ru-catalyzed transfer hydrogenation and α-methylation/transfer hydrogenation of ketones using methanol. Chinese Chemical Letters, 2024, 35(7): 109323-. doi: 10.1016/j.cclet.2023.109323
12. [12]
  Long Jin , Jian Han , Dongmei Fang , Min Wang , Jian Liao . Pd-catalyzed asymmetric carbonyl alkynylation: Synthesis of axial chiral ynones. Chinese Chemical Letters, 2024, 35(6): 109212-. doi: 10.1016/j.cclet.2023.109212
13. [13]
  Zhen Liu , Zhi-Yuan Ren , Chen Yang , Xiangyi Shao , Li Chen , Xin Li . Asymmetric alkenylation reaction of benzoxazinones with diarylethylenes catalyzed by B(C₆F₅)₃/chiral phosphoric acid. Chinese Chemical Letters, 2024, 35(5): 108939-. doi: 10.1016/j.cclet.2023.108939
14. [14]
  Xiuhua Wang , Jianrong Steve Zhou . A dicationic nickel complex-catalyzed asymmetric synthesis of chiral benzylic amines: Evolution from reductive amination to borrowing hydrogen reaction. Chinese Chemical Letters, 2026, 37(2): 111148-. doi: 10.1016/j.cclet.2025.111148
15. [15]
  Mengjun Zhao , Yuhao Guo , Na Li , Tingjiang Yan . Deciphering the structural evolution and real active ingredients of iron oxides in photocatalytic CO2 hydrogenation. Chinese Journal of Structural Chemistry, 2024, 43(8): 100348-100348. doi: 10.1016/j.cjsc.2024.100348
16. [16]
  Sanmei Wang , Dengxin Yan , Wenhua Zhang , Liangbing Wang . Graphene-supported isolated platinum atoms and platinum dimers for CO₂ hydrogenation: Catalytic activity and selectivity variations. Chinese Chemical Letters, 2025, 36(4): 110611-. doi: 10.1016/j.cclet.2024.110611
17. [17]
  Hongzhi Zhang , Hong Li , Asif Ali Haider , Junpeng Li , Zhi Xie , Hongming Jiang , Conglin Liu , Rui Wang , Jing Zhu . An unexpected role of lanthanide substitution in thermally responsive phosphors NaLnTe2O7: Eu3+ (Ln = Y and Gd). Chinese Journal of Structural Chemistry, 2025, 44(2): 100509-100509. doi: 10.1016/j.cjsc.2024.100509
18. [18]
  Zixuan Zhu , Xianjin Shi , Yongfang Rao , Yu Huang . Recent progress of MgO-based materials in CO₂ adsorption and conversion: Modification methods, reaction condition, and CO₂ hydrogenation. Chinese Chemical Letters, 2024, 35(5): 108954-. doi: 10.1016/j.cclet.2023.108954
19. [19]
  Yu Tian , Yijun Lin , Siyu Deng , Yinghe Tan , Xuanyi Bie , Zhaoyang Chen , Pangkuan Chen . Metal-Coordinate Complexes (M = 3d, 4f) with Enhanced Circularly Polarized Luminescence in Planar Chiral Pillar[5]arenes. Chinese Journal of Structural Chemistry, 2025, 44(8): 100626-100626. doi: 10.1016/j.cjsc.2025.100626
20. [20]
  Jiang Gong , Fengling Zheng , Hanqing Zhang , Weihan Shu , Hao Wang , Ni Zhang , Pengbing Huang , Chuancai Zhang , Bin Dai . The interfacial effect of SiO₂-Ni₃Mo₃N efficiently catalyzes the low-temperature hydrogenation of dimethyl oxalate to ethanol. Chinese Chemical Letters, 2025, 36(8): 111122-. doi: 10.1016/j.cclet.2025.111122