Citation: Zi-Fa Shi, Shuai-Nan Liu, Jia-Lin Zhao, Xiao-Ping Cao. Inherently Chiral Compounds[J]. University Chemistry, ;2024, 39(1): 95-104. doi: 10.3866/PKU.DXHX202306015 shu

Inherently Chiral Compounds

State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, China

Corresponding author: Zi-Fa Shi, Xiao-Ping Cao,
Received Date: 5 June 2023

Chirality research holds paramount theoretical significance and practical prospects in the field of organic chemistry. With the advancement of science and technology and the deepening of our understanding, a plethora of new concepts and techniques continue to emerge. Inherent chirality arises from the introduction of a curvature in an ideal planar structure that is devoid of perpendicular symmetry planes in its bidimensional representation, distinguished from conventional central, axial, planar, and helical chirality. It possesses unique stereochemistry and offers extensive application prospects. This review focuses on the structural characteristics, synthesis, and separation of naturally occurring inherent chiral compounds, synthetically derived chiral calixarenes, pillararenes, cyclotriveratrylenes, tribenzotriquinacenes, saddle-shaped octatomic rings, sumanenes, and cage compounds. Furthermore, it sheds light on future developmental directions and new opportunities in this domain.
- Inherently chirality,
- Compounds,
- Structure,
- Synthesis,
- Resolution
1. [1]
  Böhmer, V.; Kraft, D.; Tabatabi, M. J. Incl. Phenom. Mol. Recognit. Chem. 1994, 19 (1), 17.
2. [2]
  Cort, A. D.; Mandolini, L.; Pasquini, C.; Schiaffino, L. New J. Chem. 2004, 28 (10), 1198.
3. [3]
  Szumna, A. Chem. Soc. Rev. 2010, 39 (11), 4274.
4. [4]
5. [5]
  Shinkai, S.; Arimura, T.; Kawabata, H.; Murakami, H.; Araki, K.; Iwamoto, K.; Matsuda, T. J. Chem. Soc., Chem. Commun. 1990, 23, 1734.
6. [6]
  Iwamoto, K.; Yanagi, A.; Arimura, T.; Matsuda, T.; Shinkai, S. Chem. Lett. 1990, 19 (10), 1901.
7. [7]
  Xu, B.; Carroll, P. J.; Swager, T. M. Angew. Chem. Int. Ed. 1996, 35 (18), 2094.
8. [8]
  Wolff, A.; Böhmer, V.; Vogt, W.; Ugozzoli, F.; Andreetti, G. D. J. Org. Chem. 1990, 55 (22), 5665.
9. [9]
  Tong, S.; Li, J.-T.; Liang, D.-D.; Zhang, Y.-E.; Feng, Q.-Y.; Zhang, X.; Zhu, J.; Wang, M.-X. J. Am. Chem. Soc. 2020, 142 (34), 14432.
10. [10]
11. [11]
  Ogoshi, T.; Masaki, K.; Shiga, R.; Kitajima, K.; Yamagishi, T.-a. Org. Lett. 2011, 13 (5), 1264.
12. [12]
  Ogoshi, T.; Yamafuji, D.; Akutsu, T.; Naito, M.; Yamagishi, T.-a. Chem. Commun. 2013, 49 (78), 8782.
13. [13]
  Al-Azemi, T. F.; Vinodh, M.; Alipour, F. H.; Mohamod, A. A. Org. Chem. Front. 2019, 6 (5), 603.
14. [14]
  Canceill, J.; Collet, A.; Gabard, J.; Gottarelli, G.; Spada, G. P. J. Am. Chem. Soc. 1985, 107 (5), 1299.
15. [15]
  Niu, W.-X.; Wang, T.; Hou, Q.-Q.; Li, Z.-Y.; Cao, X.-P.; Kuck, D. J. Org. Chem. 2010, 75 (19), 6704.
16. [16]
  Li, Z.-M.; Li, Y.-W.; Cao, X.-P.; Chow, H.-F.; Kuck, D. J. Org. Chem. 2018, 83 (7), 3433.
17. [17]
  Wang, T.; Hou, Q.-Q.; Teng, Q.-F.; Yao, X.-J.; Niu, W.-X.; Cao, X.-P.; Kuck, D. Chem. Eur. J. 2010, 16 (41), 12412.
18. [18]
  Zhang, Z.-Q.; Ren, Q.-X.; Tian, W.-F.; Sun, W.-H.; Cao, X.-P.; Shi, Z.-F.; Chow, H.-F.; Kuck, D. Org. Lett. 2021, 23 (4), 1478.
19. [19]
  Luo, Y.; Wang, X.; Hu, W.; Peng, Y.; Wang, C.; Yu, T.; Cheng, S.; Li, J.; He, Y.; Gan, C.; et al. CCS Chem. 2023, 5 (4), 982.
20. [20]
  Higashibayashi, S.; Tsuruoka, R.; Soujanya, Y.; Purushotham, U.; Sastry, G. N.; Seki, S.; Ishikawa, T.; Toyota, S.; Sakurai, H. Bull. Chem. Soc. Jpn. 2012, 85 (4), 450.
21. [21]
  Zhou, H.; Ao, Y.-F.; Wang, D.-X.; Wang, Q.-Q. J. Am. Chem. Soc. 2022, 144 (37), 16767.
1. [1]
  Jing WU , Puzhen HUI , Huilin ZHENG , Pingchuan YUAN , Chunfei WANG , Hui WANG , Xiaoxia GU . Synthesis, crystal structures, and antitumor activities of transition metal complexes incorporating a naphthol-aldehyde Schiff base ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2422-2428. doi: 10.11862/CJIC.20240278
2. [2]
  Xinting XIONG , Zhiqiang XIONG , Panlei XIAO , Xuliang NIE , Xiuying SONG , Xiuguang YI . Synthesis, crystal structures, Hirshfeld surface analysis, and antifungal activity of two complexes Na(Ⅰ)/Cd(Ⅱ) assembled by 5-bromo-2-hydroxybenzoic acid ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1661-1670. doi: 10.11862/CJIC.20240145
3. [3]
  Jiaming Xu , Yu Xiang , Weisheng Lin , Zhiwei Miao . Research Progress in the Synthesis of Cyclic Organic Compounds Using Bimetallic Relay Catalytic Strategies. University Chemistry, 2024, 39(3): 239-257. doi: 10.3866/PKU.DXHX202309093
4. [4]
  Xiao SANG , Qi LIU , Jianping LANG . Synthesis, structure, and fluorescence properties of Zn(Ⅱ) coordination polymers containing tetra-alkenylpyridine ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2124-2132. doi: 10.11862/CJIC.20240158
5. [5]
  Peng ZHOU , Xiao CAI , Qingxiang MA , Xu LIU . Effects of Cu doping on the structure and optical properties of Au₁₁(dppf)₄Cl₂ nanocluster. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1254-1260. doi: 10.11862/CJIC.20240047
6. [6]
  Xilin Zhao , Xingyu Tu , Zongxuan Li , Rui Dong , Bo Jiang , Zhiwei Miao . Research Progress in Enantioselective Synthesis of Axial Chiral Compounds. University Chemistry, 2024, 39(11): 158-173. doi: 10.12461/PKU.DXHX202403106
7. [7]
  Qiuyu Ming , Huijun Jiang , Zhihao Zhang . A Sightseeing Tour of Folic Acid Processing Plant. University Chemistry, 2024, 39(9): 11-15. doi: 10.12461/PKU.DXHX202404092
8. [8]
  Zhiwen HUANG , Qi LIU , Jianping LANG . W/Cu/S cluster-based supramolecular macrocycles and their third-order nonlinear optical responses. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 79-87. doi: 10.11862/CJIC.20240184
9. [9]
  Aidang Lu , Yunting Liu , Yanjun Jiang . Comprehensive Organic Chemistry Experiment: Synthesis and Characterization of Triazolopyrimidine Compounds. University Chemistry, 2024, 39(8): 241-246. doi: 10.3866/PKU.DXHX202401029
10. [10]
  Qianlang Wang , Jijun Sun , Qian Chen , Quanqin Zhao , Baojuan Xi . The Appeal of Organophosphorus Compounds: Clearing Their Name. University Chemistry, 2025, 40(4): 299-306. doi: 10.12461/PKU.DXHX202405205
11. [11]
  Chi Li , Jichao Wan , Qiyu Long , Hui Lv , Ying Xiong . N-Heterocyclic Carbene (NHC)-Catalyzed Amidation of Aldehydes with Nitroso Compounds. University Chemistry, 2024, 39(5): 388-395. doi: 10.3866/PKU.DXHX202312016
12. [12]
  Yihao Zhao , Jitian Rao , Jie Han . Synthesis and Photochromic Properties of 3,3-Diphenyl-3H-Naphthopyran: Design and Teaching Practice of a Comprehensive Organic Experiment. University Chemistry, 2024, 39(10): 149-155. doi: 10.3866/PKU.DXHX202402050
13. [13]
  Tianyun Chen , Ruilin Xiao , Xinsheng Gu , Yunyi Shao , Qiujun Lu . Synthesis, Crystal Structure, and Mechanoluminescence Properties of Lanthanide-Based Organometallic Complexes. University Chemistry, 2024, 39(5): 363-370. doi: 10.3866/PKU.DXHX202312017
14. [14]
  Geyang Song , Dong Xue , Gang Li . Recent Advances in Transition Metal-Catalyzed Synthesis of Anilines from Aryl Halides. University Chemistry, 2024, 39(2): 321-329. doi: 10.3866/PKU.DXHX202308030
15. [15]
  Jingjing QING , Fan HE , Zhihui LIU , Shuaipeng HOU , Ya LIU , Yifan JIANG , Mengting TAN , Lifang HE , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and anticancer activity of two complexes of dimethylglyoxime organotin. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1301-1308. doi: 10.11862/CJIC.20240003
16. [16]
  Zhen Yao , Bing Lin , Youping Tian , Tao Li , Wenhui Zhang , Xiongwei Liu , Wude Yang . Visible-Light-Mediated One-Pot Synthesis of Secondary Amines and Mechanistic Exploration. University Chemistry, 2024, 39(5): 201-208. doi: 10.3866/PKU.DXHX202311033
17. [17]
  Tingyu Zhu , Hui Zhang , Wenwei Zhang . Exploration and Practice of Ideological and Political Education in the Course of Experiments on Chemical Functional Molecules: Synthesis and Catalytic Performance Study of Chiral Mn(III)Cl-Salen Complex. University Chemistry, 2024, 39(4): 75-80. doi: 10.3866/PKU.DXHX202311011
18. [18]
  Renxiao Liang , Zhe Zhong , Zhangling Jin , Lijuan Shi , Yixia Jia . A Palladium/Chiral Phosphoric Acid Relay Catalysis for the One-Pot Three-Step Synthesis of Chiral Tetrahydroquinoline. University Chemistry, 2024, 39(5): 209-217. doi: 10.3866/PKU.DXHX202311024
19. [19]
  Yan Li , Xinze Wang , Xue Yao , Shouyun Yu . 基于激发态手性铜催化的烯烃E→Z异构的动力学拆分——推荐一个本科生综合化学实验. University Chemistry, 2024, 39(5): 1-10. doi: 10.3866/PKU.DXHX202309053
20. [20]
  Feng Han , Fuxian Wan , Ying Li , Congcong Zhang , Yuanhong Zhang , Chengxia Miao . Comprehensive Organic Chemistry Experiment: Phosphotungstic Acid-Catalyzed Direct Conversion of Triphenylmethanol for the Synthesis of Oxime Ethers. University Chemistry, 2025, 40(3): 342-348. doi: 10.12461/PKU.DXHX202405181

Get Citation

PDF

XML

Metrics

PDF Downloads(16)
Abstract views(955)
HTML views(109)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142