Research Progress of Asymmetric Synthesis of Optically Active P-Stereogenic Organophosphoryl Compounds by Chiral Induction
- Corresponding author: Miao Zhiwei, miaozhiwei@nankai.edu.cn
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
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.
(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.
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
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
Moraleda, D.; Gatineau, D.; Martin, D.; Giordano, L.; Buono, G. Chem. Commun. 2008, 3031.
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
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
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
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
Muci, A. R.; Campos, K. R.; Evans, D. A. J. Am. Chem. Soc. 1995, 117, 9075.
doi: 10.1021/ja00140a028
Wolfe, B.; Livinghouse, T. J. Am. Chem. Soc. 1998, 120, 5116.
doi: 10.1021/ja973685k
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
Jugé, S.; Genet, J. P. Tetrahedron Lett. 1989, 30, 2783.
doi: 10.1016/S0040-4039(00)99124-X
Bauduin, C.; Moulin, D.; Kaloun, E. B.; Darcel, C.; Jugé, S. J. Org. Chem. 2003, 68, 4293.
doi: 10.1021/jo026355d
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
Kolodiazhnyi, O. I. Tetrahedron Lett. 1995, 36, 3921.
doi: 10.1016/0040-4039(95)00642-P
León, T.; Riera, A.; Verdaguer, X. C. H. J. Am. Chem. Soc. 2011, 133, 5740.
doi: 10.1021/ja200988c
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
Zhang, D. H.; Yuan, C. Y. Chem. -Eur. J. 2009, 15, 4088.
doi: 10.1002/chem.v15:16
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
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
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
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
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
Jin Tong , Shuyan Yu . Crystal Engineering for Supramolecular Chirality. University Chemistry, 2024, 39(3): 86-93. doi: 10.3866/PKU.DXHX202308113
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
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
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
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
Haiying Wang , Andrew C.-H. Sue . How to Visually Identify Homochiral Crystals. University Chemistry, 2024, 39(3): 78-85. doi: 10.3866/PKU.DXHX202309004
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
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
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
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
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
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
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
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
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