P-手性膦氧化物的不对称催化合成研究进展

doi:10.6023/A20010002

化学学报 ›› 2020, Vol. 78 ›› Issue (3): 193-216.DOI: 10.6023/A20010002 上一篇下一篇

综述

P-手性膦氧化物的不对称催化合成研究进展

朱仁义^a, 廖奎^a, 余金生^a, 周剑^a,b

a 华东师范大学化学与分子工程学院上海分子治疗与新药创制工程技术研究中心上海市绿色化学与化工过程绿色化重点实验室上海 200062;
b 中国科学院上海有机化学研究所金属有机化学国家重点实验室上海 200032

投稿日期:2020-01-01 发布日期:2020-02-24
通讯作者: 余金生, 周剑 E-mail:jsyu@chem.ecnu.edu.cn;jzhou@chem.ecnu.edu.cn
作者简介:朱仁义,男,汉族,1988年出生于江苏泗阳.2008年9月至2015年6月本硕毕业于江苏师范大学有机化学专业,随后加入华东师范大学周剑教授课题组攻读博士学位,研究方向为催化不对称CuAAC构建膦手性膦氧化合物;廖奎,男,汉族,1991年出生于四川安岳.2014年本科毕业于四川师范大学,随后加入华东师范大学周剑课题组攻读博士学位,研究方向为催化不对称CuAAC构建手性三级炔丙醇;余金生,华东师范大学化学与分子工程学院青年研究员,博士生导师.2011年于江西师范大学本科毕业后加入华东师范大学周剑教授课题组,并于2016年获理学博士学位.随后在日本微生物化学研究所Masakatsu Shibasaki教授课题组进行JSPS博士后研究.于2019年初加入华东师范大学,目前研究兴趣主要是含氟手性化合物的不对称催化合成及其在药物研究中的应用;周剑,华东师范大学化学与分子工程学院教授,博士生导师.本科毕业于四川师范大学;2004年毕业于中国科学院上海有机化学研究所,获理学博士学位;先后在日本东京大学Shu Kobayashi和德国马普煤炭研究所Benjamin List课题组从事博士后研究后,于2008年底加入华东师范大学.研究兴趣在于立足协同催化的理念,结合新催化剂和新试剂的设计开发,发展导向具有手性季碳的药物优势骨架的不对称催化构建新方法.
基金资助:
项目受国家自然科学基金（Nos.21725203，21901074）资助.

Recent Advances in Catalytic Asymmetric Synthesis of P-Chiral Phosphine Oxides

Zhu Ren-Yi^a, Liao Kui^a, Yu Jin-Sheng^a, Zhou Jian^a,b

a Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai 200062;
b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, CAS, Shanghai 200032

Received:2020-01-01 Published:2020-02-24
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21725203, 21901074).

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摘要/Abstract

P-手性膦氧类化合物在药物化学、有机合成化学、生命及材料科学等领域具有重要的应用价值和潜能，是一类受到广泛关注的优势结构.近年来，针对这一结构的不对称催化构建取得了显著进展.本综述旨在从三级膦氧化物的去对称化反应和（动态）动力学拆分反应以及二级膦氧化物参与的不对称反应三种策略出发，介绍目前用于构建P-手性膦氧化物的不对称催化合成方法及最新研究进展.藉此也对这些反应的机理及其优势与不足之处进行简要讨论，为从事有机合成和有机膦化学相关的研究人员提供一些有益参考和借鉴.

关键词: P-手性膦氧化物, 不对称催化合成, 去对称化反应, (动态)动力学拆分, 三级膦氧化物, 二级膦氧化物

P-Chiral phosphine oxides are a class of privileged structures, which have important applications in the field of medicinal chemistry, organic synthesis, life and material science. Recent years have witnessed significant progress in the catalytic asymmetric construction of such scaffolds. These advances are summarized in this review according to the following three major strategies:desymmetrization of prochiral tertiary phosphine oxides, (dynamic) kinetic resolution of tertiary phosphine oxides, and catalytic asymmetric reactions involving secondary phosphine oxides, and discusses the possible reaction mechanism, the advantage and disadvantage of each type of reactions, which would provide reference and inspiration for the researchers engaged in organic synthesis and organic phosphorus chemistry.

Key words: P-chiral phosphine oxide, catalytic asymmetric synthesis, desymmetrization, (dynamic) kinetic resolution, tertiary phosphine oxide, secondary phosphine oxide

引用此文

朱仁义, 廖奎, 余金生, 周剑. P-手性膦氧化物的不对称催化合成研究进展[J]. 化学学报, 2020, 78(3): 193-216.

Zhu Ren-Yi, Liao Kui, Yu Jin-Sheng, Zhou Jian. Recent Advances in Catalytic Asymmetric Synthesis of P-Chiral Phosphine Oxides[J]. Acta Chimica Sinica, 2020, 78(3): 193-216.

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参考文献

[1] (a) Dutartre, M.; Bayardon, J.; Jugé, S. Chem. Soc. Rev. 2016, 45, 5771.
(b) Macia, E. Chem. Soc. Rev. 2005, 34, 691.
[2] (a) Kazemi, M.; Tahmasbi, A. M.; Valizadeh, R.; Naserian, A. A.; Soni, A. Agric. Sci. Res. J. 2012, 2, 512.
(b) Lamberth, C. Tetrahedron 2010, 66, 7239.
[3] De Clercq, E. Clin. Microbiol. Rev. 2003, 16, 569.
[4] (a) Akiyama, T. Chem. Rev. 2007, 107, 5744.
(b) Milo, A.; Neel, A. J.; Toste, F. D.; Sigman, M. S. Science 2015, 347, 737.
[5] Duffy, M. P.; Delaunay, W.; Bouit, P.-A.; Hissler, M. Chem. Soc. Rev. 2016, 45, 5296.
[6] Ohmaru, Y.; Sato, N.; Mizutani, M.; Kotani, S.; Sugiura, M.; Nakajima, M. Org. Biomol. Chem. 2012, 10, 4562.
[7] Takaya, H.; Mashima, K.; Koyano, K.; Yagi, M.; Kumobayashi, H.; Taketomi, T.; Akutagawa, S.; Noyori, R. J. Org. Chem. 1986, 51, 629.
[8] Xu, B.; Zhu, S.-F.; Xie, X.-L, Shen, J.-J.; Zhou, Q.-L. Angew. Chem., Int. Ed. 2011, 50, 11483.
[9] Pye, P. J.; Rossen, K.; Reamer, R. A.; Tsou, N. N.; Volante, R. P.; Reider, P. J. J. Am. Chem. Soc. 1997, 119, 6207.
[10] Schulze, C. J.; Navarro, G.; Ebert, D.; DeRisi, J.; Linington, R. G. J. Org. Chem. 2015, 80, 1312.
[11] Cholongitas, E.; Papatheodoridis, G. V. Ann. Gastroenterol. 2014, 27, 331.
[12] Clarion, L.; Jacquard, C.; Sainte-Catherine, O.; Loiseau, S.; Filippini, D.; Hirlemann, M.-H.; Volle, J.-N.; Virieux, D.; Lecouvrey, M.; Pirat, J.-L.; Bakalara, N. J. Med. Chem. 2012, 55, 2196.
[13] (a) Baraniak, J.; Kinas, R. W.; Lesiak, K.; Stec, W. J. J. Chem. Soc. 1979, 940.
(b) Dostmann, W. R. G.; Taylor, S. S.; Genieser, H.-G.; Jastorff, B.; Døskeland, S. O.; Øgreid, D. J. Biol. Chem. 1990, 265, 10484.
[14] Matsukawa, M.; Sugama, H.; Imamoto, T. Tetrahedron Lett. 2000, 41, 6461.
[15] (a) Iseki, K.; Kuroki, Y.; Takahashi, M.; Kobayashi, Y. Tetrahedron Lett. 1996, 37, 5149.
(b) Iseki, K.; Kuroki, Y.; Takahashi, M.; Kishimoto, S. Tetrahedron 1997, 53, 3513.
[16] Xu, G.; Senanayake, C. H.; Tang, W. Acc. Chem. Res. 2019, 52, 1101.
[17] Selected examples using P-chiral phosphines as ligands:(a) Vineyard, B. D.; Knowles, W. S.; Sabacky, M. J.; Bachman, G. L.; Weinkauff, D. J. J. Am. Chem. Soc. 1977, 99, 5946.
(b) Gridnev, I. D.; Higashi, N.; Asakura, K.; Imamoto, T. J. Am. Chem. Soc. 2000, 122, 7183.
(c) Tang, W.; Zhang, X. Angew. Chem., Int. Ed. 2002, 41, 1612.
(d) Taylor, A. M.; Altman, R. A.; Buchwald S. L. J. Am. Chem. Soc. 2009, 131, 9900.
(e) Imamoto, T.; Tamura, K.; Zhang, Z.; Horiuchi, Y.; Sugiya, M.; Yoshida, K.; Yanagisawa, A.; Gridnev, I. D. J. Am. Chem. Soc. 2012, 134, 1754.
(f) Liu, G.; Liu, X.; Cai, Z.; Jiao, G.; Xu, G.; Tang, W. Angew. Chem., Int. Ed. 2013, 52, 4235. Selected examples using P-chiral phosphine as organocatalysts:
(g) Sampath, M.; Loh, T.-P. Chem. Sci. 2010, 1, 739.
(h) Rémond, E.; Bayardon, J.; Takizawa, S.; Rousselin, Y.; Sasai; H.; Jugé, S. Org. Lett. 2013, 15, 1870.
(i) Takizawa, S.; Rémond, E.; Arteaga, F.; Yoshida, Y.; Sridharan, V.; Bayardon, J.; Jugé, S.; Sasai, H. Chem. Commun. 2013, 49, 8392.
(j) Henry, C. E.; Xu, Q.-H.; Fan, Y.-C.; Martin, T. J.; Belding, L.; Dudding, T.; Kwon, O. J. Am. Chem. Soc. 2014, 136, 11890.
[18] (a) Liu, S.; Li, Y.-M.; Wang, D.; Wei, R.; Miao, Z.-W. Chin. J. Org. Chem. 2018, 38, 341(in Chinese). (刘双, 李玉明, 王典, 魏榕, 苗志伟, 有机化学, 2018, 38, 341.)
(b) Cui, Y.-M.; Lin, Y.; Xu. L.-W. Coord. Chem. Rev. 2017, 330, 37.
(c) Li, Z.; Duan, W.-L. Chin. J. Org. Chem. 2016, 36, 1805(in Chinese). (李振, 段伟良, 有机化学, 2016, 36, 1805.)
(d) Harvey, J. S.; Gouverneur, V. Chem. Commun. 2010, 46, 7477.
(e) Glueck, D. S. Chem. Eur. J. 2008, 14, 7108.
[19] Selected examples for chiral resolution:see ref. 17a, and (a) Korpiun, O.; Lewis, R. A.; Chickos, J.; Mislow, K. J. Am. Chem. Soc. 1968, 90, 4842. For chiral auxiliaries:
(b) Berger, O.; Montchamp, J.-L. Angew. Chem., Int. Ed. 2013, 52, 11377.
(c) Han, Z. S.; Goyal, N.; Herbage, M. A.; Sieber, J. D.; Qu, B.; Xu,Y.; Li, Z.; Reeves, J. T.; Desrosiers, J.-N.; Ma, S.; Grinberg, N.; Lee, H.;Mangunuru, H. P. R.; Zhang, Y.; Krishnamurthy, D.; Lu, B. Z.; Song, J. J.;Wang, G.; Senanayake, C. H. J. Am. Chem. Soc. 2013, 135, 2474.
(d) Gwon, D.; Lee, D.; Kim, J.; Park, S.; Chang, S. Chem. Eur. J. 2014, 20, 12421. For asymmetric oxidation of tertiary phosphines:
(e) Bergin, E.; O'Connor, C. T.; Robinson, S. B.; McGarrigle, E. M.; O'Mahony, C. P.; Gilheany, D. G. J. Am. Chem. Soc. 2007, 129, 9566.
(f) Rajendran, K. V.; Kennedy, L.; Gilheany, D. G. Eur. J. Org. Chem. 2010, 5642.
(g) Nikitin, K.; Rajendran, K. V.; Müller-Bunz, H.; Gilheany, D. G. Angew. Chem., Int. Ed. 2014, 53, 1906.
[20] (a) Zeng, X.-P.; Cao, Z.-Y.; Wang, Y.-H.; Zhou, F.; Zhou, J. Chem. Rev. 2016, 116, 7330.
(b) Petersen, K. S. Tetrahedron Lett. 2015, 56, 6523.
(c) Willis, M. C. J. Chem. Soc., Perkin Trans. 11999, 1765.
[21] Nishida, G.; Noguchi, K.; Hirano, M.; Tanaka, K. Angew. Chem., Int. Ed. 2008, 47, 3410.
[22] Zheng, Y.; Guo, L.; Zi, W. Org. Lett. 2018, 20, 7039.
[23] Zhang, Y.; Zhang, F.; Chen, L.; Xu, J.; Liu, X.; Feng, X. ACS Catal. 2019, 9, 4834.
[24] Zhu, R. Y.; Chen, L.; Hu, X. S.; Zhou, F.; Zhou, J. Chem. Sci. 2020, 11, 97.
[25] (a) Meng, J.-C.; Fokin, V. V.; Finn, M. G. Tetrahedron Lett. 2005, 46, 4543.
(b) Stephenson, G. R.; Buttress, J. P.; Deschamps, D.; Lancelot, M.; Martin, J. P.; Sheldon, A. I. G.; Alayrac, C.; Gau-mont, A.-C.; Page, P. C. B. Synlett 2013, 24, 2723.
(c) Song, T.; Li, L.; Zhou, W.; Zheng, Z.-J.; Deng, Y.; Xu, Z.; Xu, L.-W. Chem. Eur. J. 2015, 21, 554.
(d) Chen, M.-Y.; Song, T.; Zheng, Z.-J.; Xu, Z.; Cui, Y.-M.; Xu, L.-W. RSC Adv. 2016, 6, 58698.
(e) Chen, M.-Y.; Xu, Z.; Chen, L.; Song, T.; Zheng, Z.-J.; Cao, J.; Cui, Y.-M., Xu, L.-W. ChemCatChem 2018, 10, 280. For achiral version:
(f) Rodionov, V. O.; Fokin, V. V.; Finn, M. G. Angew. Chem., Int. Ed. 2005, 44, 2210.
[26] (a) Worrell, B. T.; Malik, J. A.; Fokin, V. V. Science 2013, 340, 457.
(b) Díez, J.; Gamasa, M. P.; Panera, M. Inorg. Chem. 2006, 45, 10043.
[27] Zhou, F.; Tan, C.; Tang, J.; Zhang, Y.-Y.; Gao, W.-M.; Wu, H.-H.; Yu, Y.-H.; Zhou, J. J. Am. Chem. Soc. 2013, 135, 10994.
[28] (a) Osako, T.; Uozumi, Y. Org. Lett. 2014, 16, 5866.
(b) Osako, T.; Uozumi, Y. Synlett 2015, 26, 1475.
[29] For reviews:(a) Ren, Y.; Baumgartner, T. Dalton Trans. 2012, 41, 7792.
(b) Matano, Y.; Imahori, H. Org. Biomol. Chem. 2009, 7, 1258. For recent examples:
(c) Stolar, M.; Borau-Garcia, J.; Toonen, M.; Baumgartner, T. J. Am. Chem. Soc. 2015, 137, 3366.
(d) Yamaguchi, E.; Wang, C.; Fukazawa, A.; Taki, M.; Sato, Y.; Sasaki, T.; Ueda, M.; Sasaki, N.; Higashiyama, T.; Yamaguchi, S. Angew. Chem., Int. Ed. 2015, 54, 4539.
(e) Reus, C.; Stolar, M.; Vanderkley, J.; Nebauer, J.; Baumgartner, T. J. Am. Chem. Soc. 2015, 137, 11710.
[30] Tahara, Y.-K.; Sato, T.; Matsubara, R.; Kanyiva, K. S.; Shibata, T. Heterocycles 2016, 93, 685.
[31] Harvey, J. S.; Malcolmson, S. J.; Dunne, K. S.; Meek, S. J.; Thompson, A. L.; Schrock, R. R.; Hoveyda, A. H.; Gouverneur, V. Angew. Chem., Int. Ed. 2009, 48, 762.
[32] Wang, Z.; Hayashi. T. Angew. Chem., Int. Ed. 2018, 57, 1702.
[33] For selected reviews on C-H bond functionalization, see:(a) Kakiuchi, F.; Murai, S. Acc. Chem. Res. 2002, 35, 826.
(b) Giri, R.; Shi, B.-F.; Engle, K. M.; Maugel, N.; Yu, J.-Q. Chem. Soc. Rev. 2009, 38, 3242.
(c) Xu, L.-M.; Li, B.-J.; Yang, Z.; Shi, Z.-J. Chem. Soc. Rev. 2010, 39, 712.
(d) Albrecht, M. Chem. Rev. 2010, 110, 576.
(e) Song, G.; Wang, F.; Li, X. Chem. Soc. Rev. 2012, 41, 3651.
(f) Newton, C. G.; Wang, S.-G.; Oliveira, C. C.; Cramer, N. Chem. Rev. 2017, 117, 8908.
[34] Du, Z.-J.; Guan, J.; Wu, G.-J.; Xu, P.; Gao, L.-X.; Han, F.-S. J. Am. Chem. Soc. 2015, 137, 632.
[35] Guan, J.; Wu, G.-J.; Han, F.-S. Chem. Eur. J. 2014, 20, 3301.
[36] (a) Shi, B.-F.; Maugel, N.; Zhang, Y.-H.; Yu, J.-Q. Angew. Chem., Int. Ed. 2008, 47, 4882.
(b) Shi, B.-F.; Zhang, Y.-H.; Lam, J.-K.; Wang, D.-H.; Yu, J.-Q. J. Am. Chem. Soc. 2010, 132, 460.
(c) Yang, Y.-F.; Hong, X.; Yu, J.-Q.; Houk, K. N. Acc. Chem. Res. 2017, 50, 2853.
[37] Sun, Y.; Cramer, N. Angew. Chem., Int. Ed. 2017, 56, 364.
[38] Gwon, D.; Park, S.; Chang, S. Tetrahedron 2015, 71, 4504.
[39] Jang, Y.-S.; Dieckmann, M.; Cramer, N. Angew. Chem., Int. Ed. 2017, 56, 15088.
[40] Jang, Y.-S.; Woźniak, Ł.; Pedroni, J.; Cramer, N. Angew. Chem., Int. Ed. 2018, 57, 12901.
[41] Lin, Z.-Q.; Wang, W.-Z.; Yan, S.-B.; Duan, W.-L. Angew. Chem., Int. Ed. 2015, 54, 6265.
[42] Liu, L.; Zhang, A.-A.; Wang, Y.; Zhang, F.; Zuo, Z.; Zhao, W.-X.; Feng, C.-L.; Ma, W. Org. Lett. 2015, 17, 2046.
[43] Lin, Y.; Ma, W.-Y.; Sun, Q.-Y.; Cui, Y.-M.; Xu, L.-W. Synlett 2017, 28, 1432.
[44] Li, Z.; Lin, Z.-Q.; Yan, C.-G.; Duan, W.-L. Organometallics 2019, 38, 3916.
[45] Xu, G. Q.; Li, M. H.; Wang, S. L.; Tang, W. J. Org. Chem. Front. 2015, 2, 1342.
[46] Huang, Z.; Huang, X.; Li, B.; Mou, C.; Yang, S.; Song, B.-A.; Chi, Y. R. J. Am. Chem. Soc. 2016, 138, 7524.
[47] Yang, G.-H.; Li, Y.; Li, X.; Cheng, J.-P. Chem. Sci. 2019, 10, 4322.
[48] Toda, Y.; Pink, M.; Johnston, J. N. J. Am. Chem. Soc. 2014, 136, 14734.
[49] Dobish, M. C.; Johnston, J. N. J. Am. Chem. Soc. 2011, 134, 6068.
[50] Trost, B. M.; Spohr, S. M.; Rolka, A. B.; Kalnmals, C. A. J. Am. Chem. Soc. 2019, 141, 14098.
[51] Liu, S.; Zhang, Z. F.; Xie, F.; Butt, N. A.; Sun, L.; Zhang, W. B. Tetrahedron Asymmetry 2012, 23, 329.
[52] Sun, Y.; Cramer, N. Chem. Sci. 2018, 9, 2981.
[53] Lim, K. M.-H.; Hayashi, T. J. Am. Chem. Soc. 2017, 139, 8122.
[54] Emmick, T. L.; Letsinger, R. L. J. Am. Chem. Soc. 1968, 90, 3459.
[55] Fu, X.; Loh, W.-T.; Zhang, Y.; Chen, T.; Ma, T.; Liu, H.; Wang, J.; Tan, C.-H. Angew. Chem., Int. Ed. 2009, 48, 7387.
[56] Xie, P. Z.; Guo, L.; Xu, L. L.; Loh, T.-P. Chem. Asian J. 2016, 11, 1353.
[57] (a) Zhang, H.; Sun, Y.-M.; Yao, L.; Ji, S.-Y.; Zhao, C.-Q.; Han, L.-B. Chem. Asian J. 2014, 9, 1329.
(b) Wang, J.-P.; Nie, S.-Z.; Zhou, Z.-Y.; Ye, J.-J.; Wen, J.-H.; Zhao, C.-Q. J. Org. Chem. 2016, 81, 7644.
[58] Du, J.-Y.; Ma, Y.-H.; Yuan, R.-Q.; Xin, N. N.; Nie, S.-Z.; Ma, C.-L.; Li, C.-Z.; Zhao, C.-Q. Org. Lett. 2018, 20, 477.
[59] Beaud, R.; Phipps, R. J.; Gaunt, M. J. J. Am. Chem. Soc. 2016, 138, 13183.
[60] Zhang, Y.; He, H.; Wang, Q. Y.; Cai, Q. Tetrahedron Lett. 2016, 57, 5308.
[61] Dai, Q.; Li, W.-B.; Li, Z.-M.; Zhang, J.-L. J. Am. Chem. Soc. 2019, 141, 20556.
[62] Liu, X.-T.; Zhang, Y.-Q.; Han, X.-Y.; Sun, S.-P.; Zhang, Q.-W. J. Am. Chem. Soc. 2019, 141, 16584.

P-手性膦氧化物的不对称催化合成研究进展

Recent Advances in Catalytic Asymmetric Synthesis of P-Chiral Phosphine Oxides

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