Citation: Liu Shuang, Li Yuming, Wang Dian, Wei Rong, Miao Zhiwei. Research Progress of Asymmetric Synthesis of Optically Active P-Stereogenic Organophosphoryl Compounds by Chiral Induction[J]. Chinese Journal of Organic Chemistry, ;2018, 38(2): 341-349. doi: 10.6023/cjoc201708040 shu

Research Progress of Asymmetric Synthesis of Optically Active P-Stereogenic Organophosphoryl Compounds by Chiral Induction

Liu Shuang ^a ,
Li Yuming ^a ,
Wang Dian ^a ,
Wei Rong ^a ,
Miao Zhiwei ^a,b,,

a.
State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071
b.
Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology Ministry of Education, Tsinghua. University, Beijing 100084

Corresponding author: Miao Zhiwei, miaozhiwei@nankai.edu.cn
Received Date: 20 August 2017
Revised Date: 24 September 2017
Available Online: 16 February 2017
Fund Project: Project supported by the National Key Research and Development Program of China (No. 2016YFD0201200)the National Key Research and Development Program of China 2016YFD0201200

Figures(20)

Organo-phosphorus chemistry is an important branch of organic chemistry and life science research. P-Stereogenic organophosphorus compounds have attracted great interest due to their potential applications in the fields of pharmaceutical chemistry, agrochemistry, material science and as ligands for asymmetric catalysis. The preparation of enantiomerically enriched phosphorus compounds with P-stereogenic centers using natural chiral compounds as chiral auxiliary has received considerable attention. The recent development of the asymmetric synthesis of P-stereogenic organophosphoryl compounds employing menthol, sparteine, ephedrine, and carbohydrates as chiral auxiliary is summarized.
- P-stereogenic organophosphorus compound,
- chiral induction,
- asymmetric synthesis
1. [1]
2. [2]
3. [3]
  For recent examples: (a) Geer, A. M. ; Serrano, A. L. ; de Bruin, B. ; Ciriano, M. A. ; Tejel, C. Angew. Chem., Int. Ed. 2015, 54, 472.
  (b) Lu, J. ; Ye, J. ; Duan, W. L. Chem. Commun. 2014, 50, 698.
  (c) Zhao, D. ; Wang, R. Chem. Soc. Rev. 2012, 41, 2095.
  (d) Xu, Q. ; Han, L. B. J. Organomet. Chem. 2011, 696, 130.
  (e) Zhang, H. ; Sun, Y. M. ; Zhao, Y. ; Zhou, Z. Y. ; Wang, J. P. ; Xin, N. ; Nie, S. Z. ; Zhao, C. Q. ; Han, L. B. Org. Lett. 2015, 17, 142.
  (f) Zhang, H. ; Sun, Y. M. ; Yao, L. ; Ji, S. Y. ; Zhao, C. Q. ; Han, L. B. Chem. Asian J. 2014, 9, 1329.
  (g) Sun, Y. M. ; Xin, N. ; Xu, Z. Y. ; Liu, L. J. ; Meng, F. J. ; Zhang, H. ; Fu, B. C. ; Liang, Q. J. ; Zheng, H. X. ; Sun, L. J. ; Zhao, C. Q. ; Han, L. B. Org. Biomol. Chem. 2014, 12, 9457.
  (h) Xie, P. Z. ; Guo, L. ; Xu, L. L. ; Loh, T. P. Chem. Asian J. 2016, 11, 1353.
4. [4]
5. [5]
  (a) Benschop, H. P. ; Platenburg, D. H. J. M. ; Meppelder, F. H. ; Boter, H. L. Chem. Commun. 1970, 33.
  (b) Bodalski, R. ; Koszuk, J. Phosphorus, Sulfur Silicon Relat. Elem. 1989, 44, 99.
  (c) Farnham, W. B. ; Murray, R. K. ; Mislow, K. J. Am. Chem. Soc. 1970, 92, 5809.
  (d) Han, L. B. JP 4649590, 2006 [Chem. Abstr. 2006, 145, 8273].
  (e) Han, L. B. ; Zhao, C. Q. ; Onozawa, S. Y. ; Tanaka, M. J. Am. Chem. Soc. 2002, 124, 3842.
  (f) Han, L. B. ; Zhao, C. Q. J. Org. Chem. 2005, 70, 10121.
6. [6]
  Zhang, H.; Sun, Y. M.; Yao, L.; Ji, S. Y.; Zhao, C. Q.; Han, L. B. Chem. Asian J. 2014, 9, 1329. doi: 10.1002/asia.v9.5
7. [7]
  Liu, S.; Li, Y. M.; Yin, Z. Y.; Yu, Q. L.; Miao, Z. W. J. Org. Chem. 2017, 82, 2481. doi: 10.1021/acs.joc.6b02877
8. [8]
  Moraleda, D.; Gatineau, D.; Martin, D.; Giordano, L.; Buono, G. Chem. Commun. 2008, 3031.
9. [9]
  Zhou, Y.; Wang, G.; Saga, Y.; Shen, R.; Goto, M.; Zhao, Y.; Han, L. B. J. Org. Chem. 2010, 75, 7924. doi: 10.1021/jo101540d
10. [10]
  Xiong, B.; Li, M.; Liu, Y.; Zhou, Y.; Zhao, C.; Goto, M.; Yin, S. F.; Han, L. B. Adv. Synth. Catal. 2014, 356, 781. doi: 10.1002/adsc.v356.4
11. [11]
  Xiong, B. Q.; Shen, R. W.; Goto, M.; Yin, S. F.; Han, L. B. Chem. -Eur. J. 2012, 18, 16902. doi: 10.1002/chem.v18.52
12. [12]
  Xiong, B. Q.; Zhou, Y. B.; Zhao, C. Q.; Goto, M.; Yin, S. F.; Han, L. B. Tetrahedron 2013, 69, 9373. doi: 10.1016/j.tet.2013.09.001
13. [13]
  Muci, A. R.; Campos, K. R.; Evans, D. A. J. Am. Chem. Soc. 1995, 117, 9075. doi: 10.1021/ja00140a028
14. [14]
  Wolfe, B.; Livinghouse, T. J. Am. Chem. Soc. 1998, 120, 5116. doi: 10.1021/ja973685k
15. [15]
  Gammon, J. J.; Gessner, V. H.; Barker, G. R.; Granander, J.; Whitwood, A. C.; Strohmann, C.; O'Brien, P.; Kelly, B. J. Am. Chem. Soc. 2010, 132, 13922. doi: 10.1021/ja1060966
16. [16]
  Jugé, S.; Genet, J. P. Tetrahedron Lett. 1989, 30, 2783. doi: 10.1016/S0040-4039(00)99124-X
17. [17]
  Bauduin, C.; Moulin, D.; Kaloun, E. B.; Darcel, C.; Jugé, S. J. Org. Chem. 2003, 68, 4293. doi: 10.1021/jo026355d
18. [18]
  Han, Z. S.; Goyal, N.; Herbage, M. A.; Sieber, J. D.; Qu, B.; Xu, Y. B.; Li, Z. B.; Reeves, J. T.; Desrosiers, J. N.; Ma, S. L.; Grinberg, N.; Lee, H.; Mangunuru, H. P. R.; Zhang, Y. D.; Krishnamurthy, D.; Lu, B. Z.; Song, J. J.; Wang, G. J.; Senanayake, C. H. J. Am. Chem. Soc. 2013, 135, 2474. doi: 10.1021/ja312352p
19. [19]
  Kolodiazhnyi, O. I. Tetrahedron Lett. 1995, 36, 3921. doi: 10.1016/0040-4039(95)00642-P
20. [20]
  León, T.; Riera, A.; Verdaguer, X. C. H. J. Am. Chem. Soc. 2011, 133, 5740. doi: 10.1021/ja200988c
21. [21]
  Wang, Y. D.; Wang, Y. Y.; Yu, J. P.; Miao, Z. W.; Chen, R. Y. Chem. Eur. J. 2009, 15, 9290. doi: 10.1002/chem.v15:37
22. [22]
  Zhang, D. H.; Yuan, C. Y. Chem. -Eur. J. 2009, 15, 4088. doi: 10.1002/chem.v15:16
1. [1]
  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
2. [2]
  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
3. [3]
  Ke QIAO , Yanlin LI , Shengli HUANG , Guoyu YANG . Advancements in asymmetric catalysis employing chiral iridium (ruthenium) complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2091-2104. doi: 10.11862/CJIC.20240265
4. [4]
  Dongheng WANG , Si LI , Shuangquan ZANG . Construction of chiral alkynyl silver chains and modulation of chiral optical properties. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 131-140. doi: 10.11862/CJIC.20240379
5. [5]
  Qianwen Han , Tenglong Zhu , Qiuqiu Lü , Mahong Yu , Qin Zhong . 氢电极支撑可逆固体氧化物电池性能及电化学不对称性优化. Acta Physico-Chimica Sinica, 2025, 41(1): 2309037-. doi: 10.3866/PKU.WHXB202309037
6. [6]
  Jin Tong , Shuyan Yu . Crystal Engineering for Supramolecular Chirality. University Chemistry, 2024, 39(3): 86-93. doi: 10.3866/PKU.DXHX202308113
7. [7]
  Qiuting Zhang , Fan Wu , Jin Liu , Zian Lin . Chromatographic Stationary Phase and Chiral Separation Using Frame Materials. University Chemistry, 2025, 40(4): 291-298. doi: 10.12461/PKU.DXHX202405174
8. [8]
  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
9. [9]
  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
10. [10]
  Ruiying WANG , Hui WANG , Fenglan CHAI , Zhinan ZUO , Benlai WU . Three-dimensional homochiral Eu(Ⅲ) coordination polymer and its amino acid configuration recognition. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 877-884. doi: 10.11862/CJIC.20250052
11. [11]
  Haiying Wang , Andrew C.-H. Sue . How to Visually Identify Homochiral Crystals. University Chemistry, 2024, 39(3): 78-85. doi: 10.3866/PKU.DXHX202309004
12. [12]
  Keying Qu , Jie Li , Ziqiu Lai , Kai Chen . Unveiling the Mystery of Chirality from Tartaric Acid. University Chemistry, 2024, 39(9): 369-378. doi: 10.12461/PKU.DXHX202310091
13. [13]
  Weina Wang , Lixia Feng , Fengyi Liu , Wenliang Wang . Computational Chemistry Experiments in Facilitating the Study of Organic Reaction Mechanism: A Case Study of Electrophilic Addition of HCl to Asymmetric Alkenes. University Chemistry, 2025, 40(3): 206-214. doi: 10.12461/PKU.DXHX202407022
14. [14]
  Dan Liu . 可见光-有机小分子协同催化的不对称自由基反应研究进展. University Chemistry, 2025, 40(6): 118-128. doi: 10.12461/PKU.DXHX202408101
15. [15]
  Conghao Shi , Ranran Wang , Juli Jiang , Leyong Wang . The Illustration on Stereoisomers of Macrocycles Containing Multiple Chiral Centers via Tröger Base-based Macrocycles. University Chemistry, 2024, 39(7): 394-397. doi: 10.3866/PKU.DXHX202311034
16. [16]
  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
17. [17]
  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
18. [18]
  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
19. [19]
  Hong Lu , Yidie Zhai , Xingxing Cheng , Yujia Gao , Qing Wei , Hao Wei . Advancements and Expansions in the Proline-Catalyzed Asymmetric Aldol Reaction. University Chemistry, 2024, 39(5): 154-162. doi: 10.3866/PKU.DXHX202310074
20. [20]
  Runjie Li , Hang Liu , Xisheng Wang , Wanqun Zhang , Wanqun Hu , Kaiping Yang , Qiang Zhou , Si Liu , Pingping Zhu , Wei Shao . 氨基酸的衍生及手性气相色谱分离创新实验. University Chemistry, 2025, 40(6): 286-295. doi: 10.12461/PKU.DXHX202407059

Get Citation

PDF

XML

Metrics

PDF Downloads(106)
Abstract views(4153)
HTML views(808)

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