Citation: OU Guang-Chuan, LI Zhi-Zhang, ZHANG Min, YUAN Xian-You. Chiral Resolution of β-dl-Phenylalanine Using Chiral Macrocyclic Nickel(Ⅱ) Complexes[J]. Chinese Journal of Structural Chemistry, ;2014, 33(5): 707-712. shu

Chiral Resolution of β-dl-Phenylalanine Using Chiral Macrocyclic Nickel(Ⅱ) Complexes

1.
Department of Biology and Chemistry, Hunan University of Science and Engineering, Yongzhou, Hunan 425199, China

Received Date: 29 October 2013
Available Online: 23 December 2013
Fund Project: Supported by the Scientific Research Fund of Hunan Provincial Education Department (13B029, 13A030, 13CY029) (13B029, 13A030, 13CY029) the Construct Program of the Key Discipline in Hunan Province (2011-76) (2013) and the Science and Technology Innovative Research Team in Higher Educational Institutions of Hunan Province (2012-318) (2011-76)

The reactions of chiral four-coordinated nickel(Ⅱ) complex [Ni(RR-L)](ClO₄)₂/[Ni(SS-L)](ClO₄)₂ with β-dl-phenylalanine in acetonitrile/water gave a six-coordinated enantiomer of [Ni(RR-L)(β-d-HPhe)](ClO₄)₂ (1) and [Ni(SS-L)(β-l-HPhe)](ClO₄)₂ (2), respectively (L=5,5,7, 12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane, HPhe=phenylalanine). Single-crystal X-ray diffraction analyses revealed that the nickel(Ⅱ) atom displays a distorted octahedral coordination geometry by coordinating with four nitrogen atoms of L in a folded configuration, and two carboxylate oxygen atoms of β-d/l-HPhe in cis-position in both complexes. The monomers of [Ni(RR-L)(β-d-HPhe)]²⁺ and [Ni(SS-L)(β-l-HPhe)]²⁺ are connected through intermolecular hydrogen bonds to generate one-dimensional zigzag chains, respectively. The homochiral natures of 1 and 2 are confirmed by the results of CD spectroscopy.
- chiral resolution,
- macrocyclic nickel(Ⅱ) complexes,
- β-dl-phenylalanine
1. [1]
  Meng Shan , Yongmei Yu , Mengli Sun , Shuping Yang , Mengqi Wang , Bo Zhu , Junbiao Chang . Bifunctional organocatalyst-catalyzed dynamic kinetic resolution of hemiketals for synthesis of chiral ketals via hydrogen bonding control. Chinese Chemical Letters, 2025, 36(1): 109781-. doi: 10.1016/j.cclet.2024.109781
2. [2]
  Yan-E Zhang , Yingtao Jiang , Yun Zhang , Hu Wang , Zitong Wu , Rui Li , Yumiao Ma , Tao Tu . Enantioselective synthesis of bulky planar-chiral pillar[n]arenes through dynamic kinetic resolution. Chinese Chemical Letters, 2025, 36(12): 111201-. doi: 10.1016/j.cclet.2025.111201
3. [3]
  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
4. [4]
  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
5. [5]
  Xiaofei NIU , Ke WANG , Fengyan SONG , Shuyan YU . Self-assembly of [Pd₆(L)₄]⁸⁺-type macrocyclic complexes for fluorescent sensing of HSO₃^-. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1233-1242. doi: 10.11862/CJIC.20240057
6. [6]
  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
7. [7]
  Jumei Zhang , Ziheng Zhang , Gang Li , Hongjin Qiao , Hua Xie , Ling Jiang . Ligand-mediated reactivity in CO oxidation of yttrium-nickel monoxide carbonyl complexes. Chinese Chemical Letters, 2025, 36(2): 110278-. doi: 10.1016/j.cclet.2024.110278
8. [8]
  Zhenghua ZHAO , Yufeng LIU , Qing ZHANG , Zifa SHI , Jinzhong GU . Syntheses, crystal structures, catalytic and anti-wear properties of zinc(Ⅱ), nickel(Ⅱ) and cadmium(Ⅱ) complexes constructed from a terphenyl-tricarboxylate ligand. Chinese Journal of Inorganic Chemistry, 2026, 42(1): 170-180. doi: 10.11862/CJIC.20250161
9. [9]
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10. [10]
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11. [11]
  Zhiwen Li , Jingjing Zhang , Gao Li . Dynamic assembly of chiral golden knots. Chinese Journal of Structural Chemistry, 2024, 43(7): 100300-100300. doi: 10.1016/j.cjsc.2024.100300
12. [12]
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13. [13]
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14. [14]
  Xinguo Mao , Shuo Zhang , Qiang Shi , Hua Cheng , Leyong Wang . Macrocyclic host molecules: Rising as a promising supramolecular material. Chinese Chemical Letters, 2025, 36(6): 110950-. doi: 10.1016/j.cclet.2025.110950
15. [15]
  Hao Chang , Renzhong Qiao , Chao Li . Recent advances in functionalized macrocyclic polyamines for medicine applications. Chinese Chemical Letters, 2025, 36(7): 110675-. doi: 10.1016/j.cclet.2024.110675
16. [16]
  Fuxing Yang , Mengjie Gong , Yifei Zhang , Bangchi Wei , Nan Huang , Jun Jiang . Organocatalytic enantioselective construction of axially chiral phosphorodithiolated styrenes. Chinese Chemical Letters, 2026, 37(1): 111219-. doi: 10.1016/j.cclet.2025.111219
17. [17]
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18. [18]
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19. [19]
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20. [20]
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