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]
  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
2. [2]
  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
3. [3]
  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
4. [4]
  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
5. [5]
  Lifang HE , Wenjie TANG , Yaoze LUO , Mingsheng LIANG , Jianxin TANG , Yuxuan WU , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and anticancer activity of two dialkyltin complexes constructed based on 2, 2′-bipyridin-6, 6′-dicarboxylic acid. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1601-1609. doi: 10.11862/CJIC.20250012
6. [6]
  Lei Feng , Ze-Min Zhu , Ying Yang , Zongbin He , Jiafeng Zou , Man-Bo Li , Yan Zhao , Zhikun Wu . Long-Pursued Structure of Au₂₃(S-Adm)₁₆ and the Unexpected Doping Effects. Acta Physico-Chimica Sinica, 2024, 40(5): 2305029-0. doi: 10.3866/PKU.WHXB202305029
7. [7]
  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
8. [8]
  Bin SUN , Heyan JIANG . Glucose-modified bis-Schiff bases: Synthesis and bio-activities in Alzheimer′s disease therapy. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1338-1350. doi: 10.11862/CJIC.20240428
9. [9]
  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
10. [10]
  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
11. [11]
  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
12. [12]
  Xinyi Zhang , Kai Ren , Yanning Liu , Zhenyi Gu , Zhixiong Huang , Shuohang Zheng , Xiaotong Wang , Jinzhi Guo , Igor V. Zatovsky , Junming Cao , Xinglong Wu . Progress on Entropy Production Engineering for Electrochemical Catalysis. Acta Physico-Chimica Sinica, 2024, 40(7): 2307057-0. doi: 10.3866/PKU.WHXB202307057
13. [13]
  Chunling Qin , Shuang Chen , Hassanien Gomaa , Mohamed A. Shenashen , Sherif A. El-Safty , Qian Liu , Cuihua An , Xijun Liu , Qibo Deng , Ning Hu . Regulating HER and OER Performances of 2D Materials by the External Physical Fields. Acta Physico-Chimica Sinica, 2024, 40(9): 2307059-0. doi: 10.3866/PKU.WHXB202307059
14. [14]
  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
15. [15]
  Yan Kong , Wei Wei , Lekai Xu , Chen Chen . Electrochemical Synthesis of Organonitrogen Compounds from N-integrated CO₂ Reduction Reaction. Acta Physico-Chimica Sinica, 2024, 40(8): 2307049-0. doi: 10.3866/PKU.WHXB202307049
16. [16]
  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
17. [17]
  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
18. [18]
  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
19. [19]
  Qianping Li , Hua Guan , Changfeng Wan , Yonghai Song , Jianwen Jiang . 大学有机化学复习课项目式教学——以“液晶化合物4-正戊基苯甲酸-4′-正戊基苯酯的合成路线设计与产品制备”为例. University Chemistry, 2025, 40(8): 100-116. doi: 10.12461/PKU.DXHX202410070
20. [20]
  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

Get Citation

PDF

XML

Metrics

PDF Downloads(18)
Abstract views(1272)
HTML views(133)

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