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
收稿日期: 2017-08-20
修回日期: 2017-09-24
网络出版日期: 2017-10-16
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
Received date: 2017-08-20
Revised date: 2017-09-24
Online published: 2017-10-16
Supported by
Project supported by the National Key Research and Development Program of China (No. 2016YFD0201200).
刘双 , 李玉明 , 王典 , 魏榕 , 苗志伟 . 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[J]. 有机化学, 2018 , 38(2) : 341 -349 . DOI: 10.6023/cjoc201708040
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.
[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.
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