Citation: Yu Yue-Na, Xu Ming-Hua. Chiral Phosphorus-Olefin Ligands for Asymmetric Catalysis[J]. Acta Chimica Sinica, ;2017, 75(7): 655-670. doi: 10.6023/A17040181 shu

Chiral Phosphorus-Olefin Ligands for Asymmetric Catalysis

Yu Yue-Na ,
Xu Ming-Hua ^*,,

State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China

Corresponding author: Xu Ming-Hua, xumh@simm.ac.cn
Received Date: 20 April 2017

Fund Project: the Program of Shanghai Academic Research Leaders 14XD1404400the National Natural Science Foundation of China 21472205the National Natural Science Foundation of China 21325209

Figures(45)

Transition-metal-catalyzed asymmetric transformations are among the most powerful and straightforward strategies to access various enantioenriched compounds.Hence, considerable efforts have been focused on the development of novel chiral ligands capable of highly efficient and enantioselective catalysis.The importance of olefin as ligand in transition-metal-catalyzed reactions wasn't realized until the report of the Zeise'salt in 1827.Nevertheless, application of chiral olefins as ligands for asymmetric catalysis has been overlooked for quite a long time owing to their relatively weak binding affinity toward the central metal.Since the groundbreaking work of Hayashi and Carreira in 2003~2004, chiral dienes as steering ligands in asymmetric catalysis have emerged as a fascinating new field.Given the weak coordination ability of olefins to transition-metals, functional groups with high coordination ability were considered to incorporate into the olefin framework to create a new type of hybrid olefin ligands for asymmetric catalysis.Over the past few years, a diverse range of hybrid olefin ligands were developed for various enantioselective transformations.Among these, phosphorus-based olefins represent a particularly interesting class of ligands since the first concept demonstration by Grützmacher in 2004, combining the strong coordinating phosphorus atom and the weak coordinating olefin into one ligand molecule.Typically, three structurally different types of phosphorus-based olefins are known in the literature, including phosphine-olefins, phosphoramidite/phosphinamidite-olefins, and phosphite/phosphinite-olefins.They have been successfully utilized in a series of transition-metal-catalyzed asymmetric reactions, such as iridium-catalyzed asymmetric hydrogenation of imines, allylic substitution; rhodium-catalyzed conjugate addition of organoboron reagents to α, β-unsaturated compounds, 1, 2-addition of organoboron reagents to imines/carbonyl compounds, intramolecular hydroacylation; and palladium-catalyzed asymmetric allylic alkylation/amination/etherification of allylic esters, as well as Suzuki-coupling reactions.In many cases, the reactions occur with high enantioselectivities, allows for access to a broad range of valuable chiral products.This paper reviews the literatures in this field and summarizes the remarkable progress and advances in the use of various P-olefins as powerful ligands for diverse transition metal-catalyzed asymmetric transformations since 2004.The aim is to offer an overview of the recent achievements in the rational design and development of new hybrid chiral olefin ligands for effective enantioselective catalysis.We hope that the current success of chiral phosphorus-olefin catalysis would provide an exciting opportunity for future exploration of chiral olefin ligands in a wide variety of asymmetric reactions.
- asymmetric catalysis,
- chiral ligand,
- olefin ligand,
- phosphorus-olefin ligand,
- asymmetric synthesis
1. [1]
2. [2]
  Zeise, W. C. Poggendorff's Ann. Phys. 1827, 9, 632.
3. [3]
  Hayashi, T.; Ueyama, K.; Tokunaga, N.; Yoshida, K. J. Am. Chem. Soc. 2003, 125, 11508. doi: 10.1021/ja037367z
4. [4]
  Fisher, C.; Defieber, C.; Suzuki, T.; Carreira, E. M. J. Am. Chem. Soc. 2004, 126, 1628. doi: 10.1021/ja0390707
5. [5]
6. [6]
  (a) Maire, P.; Deblon, S.; Breher, F.; Geier, J.; Böhler, C.; Rügger, H.; Schönberg, H.; Grützmacher, H. Chem. Eur. J. 2004, 10, 4198. (b) Thoumazet, C.; Ricard, L.; Grützmacher, H.; Floch, F. P. Chem. Commun. 2005, 41, 1592.
7. [7]
  Piras, E.; Läng, F.; Rüegger, H.; Stein, D.; Wörle, M.; Grützmacher, H. Chem. Eur. J. 2006, 12, 5849. doi: 10.1002/(ISSN)1521-3765
8. [8]
  (a) Shintani, R.; Duan, W.-L.; Nagano, T.; Okada, A.; Hayashi, T. Angew. Chem. Int. Ed. 2005, 44, 4611. (b) Duan, W.; Iwamura, H.; Shintani, R.; Hayashi, T. J. Am. Chem. Soc. 2007, 129, 2130.
9. [9]
  Kasák, P.; Arion, V. B.; Widhalm, M. Tetrahedron Asymmetry 2006, 17, 3084. doi: 10.1016/j.tetasy.2006.11.022
10. [10]
  (a) Štěpnička, P.; Císařová, I. Inorg. Chem. 2006, 45, 8785. (b) Stemmler, R, T.; Bolm, C. Synlett 2007, 9, 1365. (c) Csizmadiová, J.; Mečiarová, M.; Rakovský, E.; Horváth, B.; Šebesta, R. Eur. J. Org. Chem. 2011, 6110.
11. [11]
  Liu, Z.; Du, H. Org. Lett. 2010, 12, 3054. doi: 10.1021/ol101069y
12. [12]
  (a) Wershofen, S.; Scharf, H.-G. Synthesis 1988, 854. (b) Bell, T. W.; Ciaccio, J. A. J. Org. Chem. 1993, 58, 5153. (c) Mukai, C.; Kim, J. S.; Sonobe, H.; Hanaoka, M. J. Org. Chem. 1999, 64, 6822. (d) Pandey, G.; Kapur, M. Org. Lett. 2002, 4, 3883. (e) Pandey, G.; Kapur, M.; Khan, M. I.; Gaikwad, S. M. Org. Biomol. Chem. 2003, 1, 3321. (f) Horváth, A.; Benner, J.; Bäckvall, J.-E. Eur. J. Org. Chem. 2004, 3240.
13. [13]
  (a) Cao, Z.; Liu, Y.; Liu, Z.; Feng, X.; Zhuang, M.; Du, H. Org. Lett. 2011, 13, 2164. (b) Cao, Z.; Liu, Z.; Liu, Y.; Du, H. J. Org. Chem. 2011, 76, 6401. (c) Liu, Y.; Cao, Z.; Du, H. J. Org. Chem. 2012, 77, 4479.
14. [14]
  (a) Cai, F.; Pu, X.; Qi, X.; Lynch, V.; Radha, A.; Ready, J. M. J. Am. Chem. Soc. 2011, 133, 18066. (b) Antczak, M. I.; Cai, F.; Ready, J. M. Org. Lett. 2011, 13, 184.
15. [15]
  (a) Ogasawara, M.; Wu, W.-Y.; Arae, S.; Watanabe, S.; Morita, T.; Takahashi, T.; Kamikawa, K. Angew. Chem. Int. Ed. 2012, 51, 2951. (b) Ogasawara, M.; Tseng, Y. Y.; Arae, S.; Morita, T.; Nakaya, T.; Wu, W. Y.; Takahashi, T.; Kamikawa, K. J. Am. Chem. Soc. 2014, 136, 9377. (c) Kamikawa, K.; Tseng, Y.-Y.; Jian, J.-H.; Takahashi, T.; Ogasawara, M. J. Am. Chem. Soc. 2017, 139, 1545.
16. [16]
  (a) Alexakis, A.; Kanger, T.; Mangeney, P.; Rose-Munch, F.; Perrotey, A.; Rose, E. Tetrahedron: Asymmetry 1995, 6, 47. (b) Taniguchi, N.; Uemura, M. Tetrahedron 1998, 54, 12775.
17. [17]
  (a) Ferber, B.; Top, S.; Jaouen, G. J. Organomet. Chem.2004, 689, 4872. The chiral acetal directing group was originally introduced by Kagan for the preparation of planar-chiral ferrocene derivatives, see: (b) Riant, O.; Samuel, O.; Kagan, H. B. J. Am. Chem. Soc. 1993, 115, 5835. (c) Riant, O.; Samuel, O.; Flessner, T.; Taudien, S.; Kagan, H. B. J. Org. Chem. 1997, 62, 6733. (d) Geisler, F. M.; Helmchen, G. Synthesis 2006, 2201. (e) Wölfle, H.; Kopacka, H.; Wurst, K.; Ongania, K.-H.; Görtz, H.-H.; Preishuber-Pflügl, P.; Bildstein, B.J. Organomet. Chem. 2006, 691, 1197.
18. [18]
  Sieber, J. D.; Chennamadhavuni, D.; Fandrick, K. R.; Qu, B.; Han, Z. S.; Savoie, J. Org. Lett. 2014, 16, 5494. doi: 10.1021/ol5027798
19. [19]
  Gandi, V. R.; Lu, Y.; Hayashi, T. Tetrahedron:Asymmetry 2015, 26, 679. doi: 10.1016/j.tetasy.2015.05.004
20. [20]
  Qiu, X.-L.; Qing, F.-L. J. Org. Chem. 2005, 70, 3826. doi: 10.1021/jo050057+
21. [21]
  Yamamoto, K.; Shimizu, T.; Igawa, K.; Tomooka, K.; Hirai, G.; Suemune, H.; Usui, K. Sci. Rep. 2016, 6, 36211. doi: 10.1038/srep36211
22. [22]
  Mino, T.; Nishikawa, K.; Asano, M.; Shima, Y.; Ebisawa, T.; Yoshidaa, Y.; Sakamotoa, M. Org. Biomol. Chem. 2016, 14, 7509. doi: 10.1039/C6OB01354F
23. [23]
  Shintani, R.; Narui, Y.; Hayashi, S.; Hayashi, T. Chem. Commun. 2011, 47, 6123. doi: 10.1039/c1cc11823d
24. [24]
  (a) Defieber, C.; Ariger, M. A.; Moriel, P.; Carreira, E. M. Angew. Chem. Int. Ed. 2007, 46, 3139. (b) Lafrance, M.; Roggen, M.; Carreira, E. M. Angew. Chem. Int. Ed. 2012, 51, 3470. (c) Roggen, M.; Carreira, E. M. Angew. Chem. Int. Ed. 2011, 50, 5568. (d) Roggen, M.; Carreira, E. M. Angew. Chem. Int. Ed. 2012, 51, 8652. (e) Hamilton, J. Y.; Sarlah, D.; Carreira, E. M. Angew. Chem. Int. Ed. 2013, 52, 7532. (f) Hamilton, J. Y.; Sarlah, D.; Carreira, E. M. J. Am. Chem. Soc. 2013, 135, 994. (g) Hamilton, J. Y.; Sarlah, D.; Carreira, E. M. J. Am. Chem. Soc. 2014, 136, 3006.
25. [25]
  (a) Liu, Z.; Cao, Z.; Du, H. Org. Biomol. Chem. 2011, 9, 5369. (b) Liu, Y.; Du, H. Org. Lett. 2013, 4, 740. (c) Liu, Y.; Feng, X.; Du, H. Org. Biomol. Chem. 2015, 13, 125. (d) Li, G.; Feng, X.; Du, H. Org. Biomol. Chem. 2015, 13, 5826.
26. [26]
  Chen, Q.; Li, L.; Zhou, G.; Ma, X.; Zhang, L.; Guo, F.; Luo, Y.; Xia, W. Chem. Asian J. 2016, 11, 1518. doi: 10.1002/asia.201600143
27. [27]
  Minuth, T.; Boysen, M. M. K. Org. Lett. 2009, 11, 4212. doi: 10.1021/ol901579g
28. [28]
29. [29]
  (a) Mariz, R.; Brice o, A.; Dorta, R. Organometallics 2008, 27, 6605. (b) Drinkel, E.; Briceño, A.; Dorta, R. Organometallics2010, 29, 2503.
30. [30]
  Shintani, R.; Duan, W.-L.; Okamoto, K.; Hayashi, T. Tetrahedron:Asymmetry 2005, 16, 3400. doi: 10.1016/j.tetasy.2005.08.050
31. [31]
  (a) Schafroth, M. A.; Sarlah, D.; Krautwald, S.; Carreira, E. M. J. Am. Chem. Soc. 2012, 134, 20276. (b) Jeker, O. F.; Kravina, A. G.; Carreira, E. M. Angew. Chem. Int. Ed. 2013, 52, 12166.
32. [32]
  (a) Krautwald, S.; Sarlah, D.; Schafroth, M. A.; Carreira, E. M. Science2013, 340, 1065. (b) Krautwald, S.; Schafroth, M. A.; Sarlah, D.; Carreira, E. M. J. Am. Chem. Soc. 2014, 136, 3020.
33. [33]
  Hoffman, T. J.; Carreira, E. M. Angew. Chem. Int. Ed. 2011, 50, 10670. doi: 10.1002/anie.201104595
1. [1]
  Qilu DU , Li ZHAO , Peng NIE , Bo XU . Synthesis and characterization of osmium-germyl complexes stabilized by triphenyl ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1088-1094. doi: 10.11862/CJIC.20240006
2. [2]
  Xiaoling LUO , Pintian ZOU , Xiaoyan WANG , Zheng LIU , Xiangfei KONG , Qun TANG , Sheng WANG . Synthesis, crystal structures, and properties of lanthanide metal-organic frameworks based on 2, 5-dibromoterephthalic acid ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1143-1150. doi: 10.11862/CJIC.20230271
3. [3]
  Yingchun ZHANG , Yiwei SHI , Ruijie YANG , Xin WANG , Zhiguo SONG , Min WANG . Dual ligands manganese complexes based on benzene sulfonic acid and 2, 2′-bipyridine: Structure and catalytic properties and mechanism in Mannich reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1501-1510. doi: 10.11862/CJIC.20240078
4. [4]
  Youlin SI , Shuquan SUN , Junsong YANG , Zijun BIE , Yan CHEN , Li LUO . Synthesis and adsorption properties of Zn(Ⅱ) metal-organic framework based on 3, 3', 5, 5'-tetraimidazolyl biphenyl ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1755-1762. doi: 10.11862/CJIC.20240061
5. [5]
  Bo YANG , Gongxuan LÜ , Jiantai MA . Nickel phosphide modified phosphorus doped gallium oxide for visible light photocatalytic water splitting to hydrogen. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 736-750. doi: 10.11862/CJIC.20230346
6. [6]
  Zhuo WANG , Junshan ZHANG , Shaoyan YANG , Lingyan ZHOU , Yedi LI , Yuanpei LAN . Preparation and photocatalytic performance of CeO₂-reduced graphene oxide by thermal decomposition. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1708-1718. doi: 10.11862/CJIC.20240067
7. [7]
  Qiangqiang SUN , Pengcheng ZHAO , Ruoyu WU , Baoyue CAO . Multistage microporous bifunctional catalyst constructed by P-doped nickel-based sulfide ultra-thin nanosheets for energy-efficient hydrogen production from water electrolysis. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1151-1161. doi: 10.11862/CJIC.20230454
8. [8]
  Zhiwen HU , Weixia DONG , Qifu BAO , Ping LI . Low-temperature synthesis of tetragonal BaTiO₃ for piezocatalysis. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 857-866. doi: 10.11862/CJIC.20230462
9. [9]
  Guimin ZHANG , Wenjuan MA , Wenqiang DING , Zhengyi FU . Synthesis and catalytic properties of hollow AgPd bimetallic nanospheres. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 963-971. doi: 10.11862/CJIC.20230293
10. [10]
  Yufang GAO , Nan HOU , Yaning LIANG , Ning LI , Yanting ZHANG , Zelong LI , Xiaofeng LI . Nano-thin layer MCM-22 zeolite: Synthesis and catalytic properties of trimethylbenzene isomerization reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1079-1087. doi: 10.11862/CJIC.20240036
11. [11]
  Zhihuan XU , Qing KANG , Yuzhen LONG , Qian YUAN , Cidong LIU , Xin LI , Genghuai TANG , Yuqing LIAO . Effect of graphene oxide concentration on the electrochemical properties of reduced graphene oxide/ZnS. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1329-1336. doi: 10.11862/CJIC.20230447
12. [12]
  Zeyu XU , Anlei DANG , Bihua DENG , Xiaoxin ZUO , Yu LU , Ping YANG , Wenzhu YIN . Evaluation of the efficacy of graphene oxide quantum dots as an ovalbumin delivery platform and adjuvant for immune enhancement. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1065-1078. doi: 10.11862/CJIC.20240099
13. [13]
  Hao BAI , Weizhi JI , Jinyan CHEN , Hongji LI , Mingji LI . Preparation of Cu₂O/Cu-vertical graphene microelectrode and detection of uric acid/electroencephalogram. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1309-1319. doi: 10.11862/CJIC.20240001
14. [14]
  Peiran ZHAO , Yuqian LIU , Cheng HE , Chunying DUAN . A functionalized Eu³⁺ metal-organic framework for selective fluorescent detection of pyrene. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 713-724. doi: 10.11862/CJIC.20230355
15. [15]
  Yan LIU , Jiaxin GUO , Song YANG , Shixian XU , Yanyan YANG , Zhongliang YU , Xiaogang HAO . Exclusionary recovery of phosphate anions with low concentration from wastewater using a CoNi-layered double hydroxide/graphene electronically controlled separation film. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1775-1783. doi: 10.11862/CJIC.20240043
16. [16]
  Xin XIONG , Qian CHEN , Quan XIE . First principles study of the photoelectric properties and magnetism of La and Yb doped AlN. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1519-1527. doi: 10.11862/CJIC.20240064
17. [17]
  Jiakun BAI , Ting XU , Lu ZHANG , Jiang PENG , Yuqiang LI , Junhui JIA . A red-emitting fluorescent probe with a large Stokes shift for selective detection of hypochlorous acid. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1095-1104. doi: 10.11862/CJIC.20240002
18. [18]
  Jiaqi AN , Yunle LIU , Jianxuan SHANG , Yan GUO , Ce LIU , Fanlong ZENG , Anyang LI , Wenyuan WANG . Reactivity of extremely bulky silylaminogermylene chloride and bonding analysis of a cubic tetragermylene. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1511-1518. doi: 10.11862/CJIC.20240072
19. [19]
  Jin CHANG . Supercapacitor performance and first-principles calculation study of Co-doping Ni(OH)₂. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1697-1707. doi: 10.11862/CJIC.20240108
20. [20]
  Wenlong LI , Xinyu JIA , Jie LING , Mengdan MA , Anning ZHOU . Photothermal catalytic CO₂ hydrogenation over a Mg-doped In₂O_3-x catalyst. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 919-929. doi: 10.11862/CJIC.20230421

Get Citation

PDF

XML

Metrics

PDF Downloads(45)
Abstract views(2429)
HTML views(443)

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