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

doi:10.6023/cjoc201708040

Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (2): 341-349.DOI: 10.6023/cjoc201708040 Previous Articles Next Articles

Special Issue: 元素有机化学合辑2018-2019

Reviews

手性诱导构建磷手性中心不对称合成有机磷功能化合物研究进展

刘双^a, 李玉明^a, 王典^a, 魏榕^a, 苗志伟^a,b

a 南开大学化学学院元素有机化学国家重点实验室天津 300071;
b 清华大学生命有机磷化学及化学生物学教育部重点实验室北京 100084

收稿日期:2017-08-20 修回日期:2017-09-24 发布日期:2017-10-16
通讯作者: 苗志伟 E-mail:miaozhiwei@nankai.edu.cn
基金资助:
国家重点研发计划（No.2016YFD0201200）资助项目.

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

Received:2017-08-20 Revised:2017-09-24 Published:2017-10-16
Contact: 10.6023/cjoc201708040 E-mail:miaozhiwei@nankai.edu.cn
Supported by:
Project supported by the National Key Research and Development Program of China (No. 2016YFD0201200).

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.

Key words: P-stereogenic organophosphorus compound, chiral induction, asymmetric synthesis

Cite this article

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]. Chin. J. Org. Chem., 2018, 38(2): 341-349.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] For selected reviews see:(a) Montchamp, J. L. Acc. Chem. Res. 2014, 47, 77.
(b) Dubrovina, N. V.; Börner, A. Angew. Chem., Int. Ed. 2004, 43, 5883.
(c) Tang, C. C.; Zhou, Z. H. Organophosphorus Reagents in Asymmetric Reactions, Nankai University Press, Tianjin, 2012(in Chinese). (唐除痴, 周正洪, 不对称反应中的有机磷试剂, 南开大学出版社, 天津, 2012.)(d) Queffélec, C.; Petit, M.; Janvier, P.; Knight, D. A.; Bujoli, B. Chem. Rev. 2012, 112, 3777.
(e) Baumgartner, T.; Réau, R. Chem. Rev. 2006, 106, 4681.
(f) Dutartre, M.; Bayardon, J.; Jugé, S. Chem. Soc. Rev. 2016, 45, 5771.
[2] (a) Chen, T. Q.; Han, L. B. Synlett 2015, 26, 1153.
(b) Yao, Q. L.; Wang, A. J.; Pu, J. Z.; Tang, Y. M. Chin. J. Org. Chem. 2014, 34, 292(in Chinese). (姚秋丽, 王安俊, 蒲家志, 唐瑜敏, 有机化学, 2014, 34, 292.)
[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] (a) Lait, S. M.; Rankic, D. A.; Keay, B. A. Chem. Rev. 2007, 107, 767.
(b) Boysen, M. M. K. Carbohydrates-Tools for Stereoselective Synthesis, WILEY-VCN, Weinheim, 2013.
(c) Hu, C. F.; Cai, Y.; Abudukeremu, M.; Miao, Z. W. Chin. J. Org. Chem. 2015, 35, 2135(in Chinese). (胡辰飞, 蔡岩, 木尼热•阿布都克力木, 苗志伟, 有机化学, 2015, 35, 2135.)
[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] Zhang, H.; Sun, Y. M.; Yao, L.; Ji, S. Y.; Zhao, C. Q.; Han, L. B. Chem. Asian J. 2014, 9, 1329.
[7] Liu, S.; Li, Y. M.; Yin, Z. Y.; Yu, Q. L.; Miao, Z. W. J. Org. Chem. 2017, 82, 2481.
[8] Moraleda, D.; Gatineau, D.; Martin, D.; Giordano, L.; Buono, G. Chem. Commun. 2008, 3031.
[9] Zhou, Y.; Wang, G.; Saga, Y.; Shen, R.; Goto, M.; Zhao, Y.; Han, L. B. J. Org. Chem. 2010, 75, 7924.
[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.
[11] Xiong, B. Q.; Shen, R. W.; Goto, M.; Yin, S. F.; Han, L. B. Chem. -Eur. J. 2012, 18, 16902.
[12] Xiong, B. Q.; Zhou, Y. B.; Zhao, C. Q.; Goto, M.; Yin, S. F.; Han, L. B. Tetrahedron 2013, 69, 9373.
[13] Muci, A. R.; Campos, K. R.; Evans, D. A. J. Am. Chem. Soc. 1995, 117, 9075.
[14] Wolfe, B.; Livinghouse, T. J. Am. Chem. Soc. 1998, 120, 5116.
[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.
[16] Jugé, S.; Genet, J. P. Tetrahedron Lett. 1989, 30, 2783.
[17] Bauduin, C.; Moulin, D.; Kaloun, E. B.; Darcel, C.; Jugé, S. J. Org. Chem. 2003, 68, 4293.
[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.
[19] Kolodiazhnyi, O. I. Tetrahedron Lett. 1995, 36, 3921.
[20] León, T.; Riera, A.; Verdaguer, X. C. H. J. Am. Chem. Soc. 2011, 133, 5740.
[21] Wang, Y. D.; Wang, Y. Y.; Yu, J. P.; Miao, Z. W.; Chen, R. Y. Chem. Eur. J. 2009, 15, 9290.
[22] Zhang, D. H.; Yuan, C. Y. Chem. -Eur. J. 2009, 15, 4088.

手性诱导构建磷手性中心不对称合成有机磷功能化合物研究进展

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

PDF

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Huakun Wang, Xiaolong Ren, Yining Xuan. Study of the Halide Salt Catalyzed [3＋2] Cycloaddition of α,β-Epoxy Carboxylate with Isocyanate [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 251-258.
[2]	Shihang Yu, Jiawei Liu, Biyu An, Qinghua Bian, Min Wang, Jiangchun Zhong. Asymmetric Synthesis of the Contact Sex Pheromone of Neoclytus acuminatus acuminatus (Fabricius) [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 301-308.
[3]	Yuchao Wang, Jinbiao Liu, Zhitao He. Palladium-Catalyzed Asymmetric Hydrofunctionalizations of Conjugated Dienes [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2614-2627.
[4]	Tingyu Song, Ran Li, Lihua Huang, Shikun Jia, Guangjian Mei. Catalytic Asymmetric Synthesis of N—N Atropisomers [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 1977-1990.
[5]	Cheng Luo, Yanli Yin, Zhiyong Jiang. Recent Advances in Asymmetric Synthesis of P-Chiral Phosphine Oxides [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 1963-1976.
[6]	Ling Meng, Jun Wang. Research Progress on Synthesis of Thioflavonoids [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 873-891.
[7]	Tiantian Liu, Xinhong Duan. Recent Progress in the Construction of Chiral 3-Substituted Indoles by Asymmetric Friedel-Crafts Reactions [J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3695-3712.
[8]	Huaiyuan Zhang, Nuo Xu, Rongping Tang, Xingli Shi. Recent Advances in Asymmetric Dearomatization Reactions Induced by Chiral Hypervalent Iodine Reagents [J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3784-3805.
[9]	Liu-Yang Pu, Zhiyue Li, Limin Li, Yucui Ma, Min Ma, Shengquan Hu, Zhengzhi Wu. Asymmetric Synthesis of (–)-Colchicine and Its Natural Analog (–)-N-Acetylcolchicine Methyl Ether [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 313-319.
[10]	Yuanhao Mao, Yanfeng Gao, Zhiwei Miao. Research Progress on the Asymmetric Cyclization Synthesis of Seven-Membered Rings via Transition Metal Catalysis [J]. Chinese Journal of Organic Chemistry, 2022, 42(7): 1904-1924.
[11]	Ting Yao, Jiayan Li, Jiaming Wang, Changgui Zhao. Recent Advances for the Construction of Seven-Membered Ring Catalyzed by N-Heterocyclic Carbenes [J]. Chinese Journal of Organic Chemistry, 2022, 42(4): 925-944.
[12]	Lihua Wang, Xushun Gong, Ting Lei, Shizhi Jiang. Research Progress on Asymmetric Synthesis of Flavanones [J]. Chinese Journal of Organic Chemistry, 2022, 42(3): 758-769.
[13]	Yiwen Su, Youquan Zou, Wenjing Xiao. Recent Advances in Photocatalytic Deracemization [J]. Chinese Journal of Organic Chemistry, 2022, 42(10): 3201-3212.
[14]	Xiuliang Cheng, Dong Li, Boxuan Yang, Yumei Lin, Lei Gong. Recent Advances in Visible-Light Photocatalytic Asymmetric Synthesis Enabled by Chiral Lewis Acids [J]. Chinese Journal of Organic Chemistry, 2022, 42(10): 3335-3350.
[15]	Xudong Hu, Xinliang Zhang, Wenbo Liu. Advances of Chiral Spiro Skeleton-Based Bisnitrogen Ligands in Transition-Metal Catalysis [J]. Chinese Journal of Organic Chemistry, 2022, 42(10): 3102-3117.