Citation: Wang Su, Zhang Youlu, Ba Yanyan, Zhang Jingyu, Sun Demei. Study and Applications of Stereoselective Olefin Metathesis Reactions[J]. Chinese Journal of Organic Chemistry, ;2020, 40(9): 2725-2741. doi: 10.6023/cjoc202003054 shu

Study and Applications of Stereoselective Olefin Metathesis Reactions

College of Pharmacy, Henan University of Chinese Medicine, Zhengzhou 450046

Corresponding author: Sun Demei, muzhi527@163.com
Received Date: 23 March 2020
Revised Date: 10 May 2020
Available Online: 25 May 2020
Fund Project: Project supported by the Science & Technology Innovation Talents of Henan University of Chinese Medicine (No. 2014XCXRC01) and the Henan University of Chinese Medicine, Provincial Scientific Research Business (No. 2014KYYWF-ZZCX3-05)the Henan University of Chinese Medicine, Provincial Scientific Research Business 2014KYYWF-ZZCX3-05the Science & Technology Innovation Talents of Henan University of Chinese Medicine 2014XCXRC01

Figures(27)

Olefin metathesis has been one of the most important methods to construct carbon-carbon double bonds, which has been catalyzed by ruthenium carbene. Investigations in olefin metathesis have focused on stereoselective transformations in recent years. The research progress on the applications of stereoselective olefin metathesis reactions catalyzed by ruthenium carbene complexes is reviewed. The advancements in stereoselectivity of olefin metathesis are described in detail, and the categories and improvement of ruthenium catalysts are also introduced over the past decade. Finally, the future development for olefin metathesis is further evaluated as well.
- olefin metathesis,
- ruthenium,
- catalyst,
- stereoselective
1. [1]
  Jean-Louis, H. P.; Chauvin, Y. Makromol. Chem. 1971, 141, 161. doi: 10.1002/macp.1971.021410112
2. [2]
  Keitz, B. K.; Endo, K.; Patel, P. R.; Herbert, M. B.; Grubbs, R. H. J. Am. Chem. Soc. 2012, 134, 693. doi: 10.1021/ja210225e
3. [3]
  Marx, V. M.; Herbert, M. B.; Keitz, B. K.; Grubbs, R. H. J. Am. Chem. Soc. 2013, 135, 94. doi: 10.1021/ja311241q
4. [4]
  Rosebrugh, L. E.; Herbert, M. B.; Marx, V. M.; Keitz, B. K.; Grubbs, R. H. J. Am. Chem. Soc. 2013, 135, 1276. doi: 10.1021/ja311916m
5. [5]
  Ahmed, T. S.; Grubbs, R. H. Angew. Chem.. Int. Ed. 2017, 56, 11213. doi: 10.1002/anie.201704670
6. [6]
  Khan, R. K. M.; Zhugralin, A. R.; Torker, S.; O'Brien, R. V.; Lombardi, P. J.; Hoveyda, A. H. J. Am. Chem. Soc. 2012, 134, 12438. doi: 10.1021/ja3056722
7. [7]
  Khan, R. K. M.; O'Brien, R. V.; Torker, S.; Li, B.; Hoveyda, A. H. J. Am. Chem. Soc. 2012, 134, 12774. doi: 10.1021/ja304827a
8. [8]
  Hartung, J.; Grubbs, R. H. J. Am. Chem. Soc. 2013, 135, 10183. doi: 10.1021/ja4046422
9. [9]
  Luo, S. X.; Cannon, J. S.; Taylor, B. L. H.; Engle, K. M.; Houk, K. N.; Grubbs, R. H. J. Am. Chem. Soc. 2016, 138, 14039. doi: 10.1021/jacs.6b08387
10. [10]
  Keitz, B. K.; Endo, K.; Herbert, M. B.; Grubbs, R. H. J. Am. Chem. Soc. 2011, 133, 9686. doi: 10.1021/ja203488e
11. [11]
  Endo, K.; Grubbs, R. H. J. Am. Chem. Soc. 2011, 133, 8525. doi: 10.1021/ja202818v
12. [12]
  Bronner, S. M.; Herbert, M. B.; Patel, P. R.; Marx, V. M.; Grubbs, R. H. Chem. Sci. 2014, 5, 4091. doi: 10.1039/C4SC01541J
13. [13]
  Cannon, J. S.; Grubbs, R. H. Angew. Chem.. Int. Ed. 2013, 52, 9001. doi: 10.1002/anie.201302724
14. [14]
  Quigley, B. L.; Grubbs, R. H. Chem. Sci. 2014, 5, 501. doi: 10.1039/C3SC52806E
15. [15]
  Herbert, M. B.; Grubbs, R. H. Angew. Chem.. Int. Ed. 2015, 54, 2. doi: 10.1002/anie.201410932
16. [16]
  Koh, M. J.; Khan, R. K. M.; Torker, S.; Yu, M.; Mikus, M. S.; Hoveyda, A. H. Nature 2015, 517, 181. doi: 10.1038/nature14061
17. [17]
  Tiede, S.; Berger, A.; Schlesiger, D.; Rost, D.; Lühl, A.; Blechert, S. Angew. Chem.. Int. Ed. 2010, 49, 3972. doi: 10.1002/anie.201000940
18. [18]
  Miyazaki, H.; Herbert, M. B.; Liu, P.; Dong, X.; Xu, X.; Keitz, B. K.; Ung, T.; Mkrtumyan, G.; Houk, K. N.; Grubbs, R. H. J. Am. Chem. Soc. 2013, 135, 5848. doi: 10.1021/ja4010267
19. [19]
  Johns, A. M.; Ahmed, T. S.; Jackson, B. W.; Grubbs, R. H.; Pederson, R. L. Org. Lett. 2016, 18, 772. doi: 10.1021/acs.orglett.6b00031
20. [20]
  Montgomery, T. P.; Ahmed, T. S.; Grubbs, R. H. Angew. Chem.. Int. Ed. 2017, 56, 11024. doi: 10.1002/anie.201704686
21. [21]
  Khan, R. K. M.; Torker, S.; Hoveyda, A. H. J. Am. Chem. Soc. 2013, 135, 10258. doi: 10.1021/ja404208a
22. [22]
  Ahmed, T. S.; Grubbs, R. H. J. Am. Chem. Soc. 2017, 139, 1532. doi: 10.1021/jacs.6b11330
23. [23]
  Ahmed, T. S.; Grubbs, R. H. J. Am. Chem. Soc. 2017, 139, 1532. doi: 10.1021/jacs.6b11330
24. [24]
  Xu, C. F.; Shen, X.; Hoveyda, A. H. J. Am. Chem. Soc. 2017, 139, 10919. doi: 10.1021/jacs.7b06552
25. [25]
  Xu, C. F.; Liu, Z. X.; Torker, S.; Shen, X.; Xu, D. M.; Hoveyda, A. H. J. Am. Chem. Soc. 2017, 139, 15640. doi: 10.1021/jacs.7b10010
26. [26]
  Ahmed, T. S.; Montgomery, T. P.; Grubbs, R. H. Chem. Sci. 2018, 9, 3580. doi: 10.1039/C8SC00435H
27. [27]
  Torker, S.; Khan, R. K. M.; Hoveyda, A. H. J. Am. Chem. Soc. 2014, 136, 3439. doi: 10.1021/ja410606b
28. [28]
  Khan, R. K. M.; Torker, S.; Hoveyda, A. H. J. Am. Chem. Soc. 2014, 136, 14337. doi: 10.1021/ja505961z
29. [29]
  Mikus, M. S.; Torker, S.; Xu, C.; Li, B.; Hoveyda, A. H. Organometallics 2016, 35, 3878. doi: 10.1021/acs.organomet.6b00773
30. [30]
  Montgomery, T. P.; Grandner, J. M.; Houk, K. N.; Grubbs, R. H. Organometallics 2017, 36, 3940. doi: 10.1021/acs.organomet.7b00555
31. [31]
  Dumas, A.; Müller, D. S.; Curbet, I.; Toupet, L.; Rouen, M.; Baslé, O.; Mauduit, M. Organometallics 2018, 37, 829. doi: 10.1021/acs.organomet.7b00836
32. [32]
  Seiders, T. J.; Ward, D. W.; Grubbs, R. H. Org. Lett. 2001, 3, 3225. doi: 10.1021/ol0165692
33. [33]
  Stenne, B.; Timperio, J.; Savoie, J.; Dudding, T.; Collins, S. K. Org. Lett. 2010, 12, 2032. doi: 10.1021/ol100511d
34. [34]
  Gawin, R.; Pieczykolan, M.; Malinska, M.; Wozniak, K.; Grela, K. Synlett 2013, 24, 1250. doi: 10.1055/s-0033-1338877
35. [35]
  Paradiso, V.; Bertolasi, V.; Grisi, F. Organometallics 2014, 33, 5932. doi: 10.1021/om500731k
36. [36]
  Paradiso, V.; Bertolasi, V.; Costabile, C.; Grisi, F. Dalton Trans. 2016, 45, 561. doi: 10.1039/C5DT03758A
37. [37]
  Hartung, J.; Dornan, P. K.; Grubbs, R. H. J. Am. Chem. Soc. 2014, 136, 13029. doi: 10.1021/ja506611k
38. [38]
  Kannenberg, A.; Rost, D.; Eibauer, S.; Tiede, S.; Blechert, S. Angew. Chem.. Int. Ed. 2011, 50, 3299. doi: 10.1002/anie.201007673
39. [39]
  Hartung, J.; Grubbs, R. H. Angew. Chem.. Int. Ed. 2014, 53, 3885. doi: 10.1002/anie.201310767
40. [40]
  Berlin, J. M.; Goldberg, S. D.; Grubbs, R. H. Angew. Chem.. Int. Ed. 2006, 45, 7591. doi: 10.1002/anie.200602469
41. [41]
  Werrel, S.; Walker, J. C. L.; Donohoe, T. J. Tetrahedron Lett. 2015, 56, 5261. doi: 10.1016/j.tetlet.2015.07.008
42. [42]
  Montgomery, T. P.; Johns, A. M.; Grubbs, R. H. Catalysts 2017, 7, 87. doi: 10.3390/catal7030087
43. [43]
  Ogba, O. M.; Warner, N. C.; O'Leary, D. J.; Grubbs, R. H. Chem. Soc. Rev. 2018, 47, 4510. doi: 10.1039/C8CS00027A
44. [44]
  Potukuchi, H. K.; Colomer, I.; Donohoe, T. J. Adv. Heterocycl. Chem. 2016, 120, 43. doi: 10.1016/bs.aihch.2016.04.006
45. [45]
  Hoveyda, A. H.; Malcolmson, S. J.; Meek, S. J.; Zhugralin, A. R. Angew. Chem.. Int. Ed. 2010, 49, 34. doi: 10.1002/anie.200904491
46. [46]
  Donohoe, T. J.; Jones, C. R.; Barbosa, L. C. A. J. Am. Chem. Soc. 2011, 133, 16418. doi: 10.1021/ja207835w
47. [47]
  Song, W.; Wang, Y.; Qu, J.; Lin, Q. J. Am. Chem. Soc. 2008, 130, 9654. doi: 10.1021/ja803598e
48. [48]
  Van Hest, J. C. M.; Kiick, K. L.; Tirrell, D. A. J. Am. Chem. Soc. 2000, 122, 1282. doi: 10.1021/ja992749j
49. [49]
  Bernardes, G. J. L.; Chalker, J. M.; Errey, J. C.; Davis, B. G. J. Am. Chem. Soc. 2008, 130, 5052. doi: 10.1021/ja800800p
50. [50]
  Lin, Y. A.; Boutureira, O.; Lercher, L.; Bhushan, B.; Paton, R. S.; Davis, B. G. J. Am. Chem. Soc. 2013, 135, 12156. doi: 10.1021/ja403191g
51. [51]
  Zhu, Y.; van der Donk, W. A. Org. Lett. 2001, 3, 1189. doi: 10.1021/ol015648a
52. [52]
  Mangold, S. L.; O'Leary, D. J.; Grubbs, R. H. J. Am. Chem. Soc. 2014, 136, 12469. doi: 10.1021/ja507166g
53. [53]
  Mangold, S. L.; Grubbs, R. H. Chem. Sci. 2015, 6, 4561. doi: 10.1039/C5SC01507C
54. [54]
  Silverstein, R. M.; Brownlee, R. G.; Bellas, T. E.; Wood, D. L.; Browne, L. E. Science 1968, 159, 889. doi: 10.1126/science.159.3817.889
55. [55]
  Henrick, C. A. Tetrahedron 1977, 33, 1845. doi: 10.1016/0040-4020(77)80372-4
56. [56]
  Ortiz, A.; Quesada, A.; Sanchez, A. J. Chem. Ecol. 2004, 30, 991. doi: 10.1023/B:JOEC.0000028463.43564.40
57. [57]
  Howse, P. E.; Stevens, I. D. R.; Jones, O. T. Insect Pheromones and their Use in Pest Management, Springer, Dordrecht, Netherlands, 1998.
58. [58]
  Herbert, M. B.; Marx, V. M.; Pederson, R. L.; Grubbs, R. H. Angew. Chem.. Int. Ed. 2013, 52, 310. doi: 10.1002/anie.201206079
59. [59]
  Ando, T.; Inomata, S.; Yamamoto, M. In Topics in Current Chemistry, Ed.: Schulz, S., Springer, Berlin/Heidelberg, 2004, pp. 51~96.
60. [60]
  Ciminiello, P.; Fattorusso, E.; Forino, M.; Di Rosa, M.; Ianaro, A.; Poletti, R. J. Org. Chem. 2001, 66, 578. doi: 10.1021/jo001437s
61. [61]
  Ciminiello, P.; Dell'Aversano, C.; Fattorusso, E.; Forino, M.; Magno, S.; Di Rosa, M.; Ianaro, A.; Poletti, R. J. Am. Chem. Soc. 2002, 124, 13114. doi: 10.1021/ja0207347
62. [62]
  Ciminiello, P.; Dell'Aversano, C.; Fattorusso, E.; Forino, M.; Magno, S.; Di Meglio, P.; Ianaro, A.; Poletti, R. Tetrahedron 2004, 60, 7093. doi: 10.1016/j.tet.2003.12.072
63. [63]
  Chung, W.; Carlson, J. S.; Bedke, D. K.; Vanderwal, C. D. Angew. Chem.. Int. Ed. 2013, 52, 10052. doi: 10.1002/anie.201304565
64. [64]
  Dornan, P. K.; Wickens, Z. K.; Grubbs, R. H. Angew. Chem.. Int. Ed. 2015, 54, 7134. doi: 10.1002/anie.201501505
65. [65]
  Dornan, P. K.; Lee, D.; Grubbs, R. H. J. Am. Chem. Soc. 2016, 138, 6372. doi: 10.1021/jacs.6b02653
66. [66]
  Yu, M.; Schrock, R. R.; Hoveyda, A. H. Angew. Chem.. Int. Ed. 2014, 53, 1. doi: 10.1002/anie.201310509
67. [67]
  Wright, A. E.; Botelho, J. C.; Guzmán, E.; Harmody, D.; Linley, P.; McCarthy, P. J.; Pitts, T. P.; Pomponi, S. A.; Reed, J. K. J. Nat. Prod. 2007, 70, 412. doi: 10.1021/np060597h
68. [68]
  Youngsaye, W.; Lowe, J. T.; Pohlki, F.; Ralifo, P.; Panek, J. S. Angew. Chem.. Int. Ed. 2007, 46, 9211. doi: 10.1002/anie.200704122
69. [69]
  Custar, D. W.; Zabawa, T. P.; Scheidt, K. A. J. Am. Chem. Soc. 2008, 130, 804. doi: 10.1021/ja710080q
70. [70]
  Woo, S. K.; Kwon, M. S.; Lee, E. Angew. Chem.. Int. Ed. 2008, 47, 3242. doi: 10.1002/anie.200800386
71. [71]
  Fuwa, H.; Naito, S.; Goto, T.; Sasaki, M. Angew. Chem.. Int. Ed. 2008, 47, 4737. doi: 10.1002/anie.200801399
72. [72]
  Paterson, I.; Miller, N. A. Chem. Commun. 2008, 4708.
73. [73]
  Guinchard, X.; Roulland, E. Org. Lett. 2009, 11, 4700. doi: 10.1021/ol902047z
74. [74]
  Fuwa, H.; Saito, A.; Sasaki, M. A. Angew. Chem.. Int. Ed. 2010, 49, 3041. doi: 10.1002/anie.201000624
75. [75]
  Yu, M.; Schrock, R. R.; Hoveyda, A. H. Angew. Chem.. Int. Ed. 2015, 54, 215. doi: 10.1002/anie.201409120
76. [76]
  De Léséleuc, M.; Godin, É.; Parisien-Collette, S.; Lévesque, A.; Collins, S. K. J. Org. Chem. 2016, 81, 6750. doi: 10.1021/acs.joc.6b01500
77. [77]
  Zhang, B.; Wang, Y.; Yang, S. P.; Zhou, Y.; Wu, W. B.; Tang, W.; Zuo, J. P.; Li, Y.; Yue, J. M. I. J. Am. Chem. Soc. 2012, 134, 20605. doi: 10.1021/ja310482z
78. [78]
  Li, J. M.; Ahmed, T. S.; Xu, C.; Stoltz, B. M.; Grubbs, R. H. J. Am. Chem. Soc. 2019, 141, 154. doi: 10.1021/jacs.8b12816
1. [1]
  Zhi Chai , Huashan Huang , Xukai Shi , Yujing Lan , Zhentao Yuan , Hong Yan . Wittig反应的立体选择性. University Chemistry, 2025, 40(8): 192-201. doi: 10.12461/PKU.DXHX202410046
2. [2]
  Wenruo NI , Hongpeng LI , Yun ZHANG , Yiran TIAN , Jiehui RUI , Yingcheng TONG , Xiaolin PI , Zhenyan TANG . Research progress of ruthenium alloy catalysts in hydrogen evolution reaction. Chinese Journal of Inorganic Chemistry, 2026, 42(1): 23-44. doi: 10.11862/CJIC.20250188
3. [3]
  Hailang JIA , Yujie LU , Pengcheng JI . Preparation and properties of nitrogen and phosphorus co-doped graphene carbon aerogel supported ruthenium electrocatalyst for hydrogen evolution reaction. Chinese Journal of Inorganic Chemistry, 2025, 41(11): 2327-2336. doi: 10.11862/CJIC.20250021
4. [4]
  Peng YUE , Liyao SHI , Jinglei CUI , Huirong ZHANG , Yanxia GUO . Effects of Ce and Mn promoters on the selective oxidation of ammonia over V₂O₅/TiO₂ catalyst. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 293-307. doi: 10.11862/CJIC.20240210
5. [5]
  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
6. [6]
  Jiayi Yang , Jianxiu Hao , Huacong Zhou , Quansheng Liu . “Gorgeous Transformation” of Carbon Dioxide into Cyclic Carbonates: Catalyst Types and Roles. University Chemistry, 2026, 41(2): 178-189. doi: 10.12461/PKU.DXHX202502105
7. [7]
  Bing WEI , Jianfan ZHANG , Zhe CHEN . Research progress in fine tuning of bimetallic nanocatalysts for electrocatalytic carbon dioxide reduction. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 425-439. doi: 10.11862/CJIC.20240201
8. [8]
  Wentao Xu , Xuyan Mo , Yang Zhou , Zuxian Weng , Kunling Mo , Yanhua Wu , Xinlin Jiang , Dan Li , Tangqi Lan , Huan Wen , Fuqin Zheng , Youjun Fan , Wei Chen . Bimetal Leaching Induced Reconstruction of Water Oxidation Electrocatalyst for Enhanced Activity and Stability. Acta Physico-Chimica Sinica, 2024, 40(8): 2308003-0. doi: 10.3866/PKU.WHXB202308003
9. [9]
  Chenyang WANG , Yiyan BAI , Wei ZHANG , Zhaorong LIU , Yuchun WANG . Performance of photo-assisted copper oxide catalyzed hydrolysis of ammonia borane to produce hydrogen. Chinese Journal of Inorganic Chemistry, 2026, 42(1): 97-110. doi: 10.11862/CJIC.20250116
10. [10]
  Yongwei ZHANG , Chuang ZHU , Wenbin WU , Yongyong MA , Heng YANG . Efficient hydrogen evolution reaction activity induced by ZnSe@nitrogen doped porous carbon heterojunction. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 650-660. doi: 10.11862/CJIC.20240386
11. [11]
  Zhaoyu Wen , Na Han , Yanguang Li . Recent Progress towards the Production of H₂O₂ by Electrochemical Two-Electron Oxygen Reduction Reaction. Acta Physico-Chimica Sinica, 2024, 40(2): 2304001-0. doi: 10.3866/PKU.WHXB202304001
12. [12]
  Mei-Xia Yang , Zhen-Hong He , Long-Rui Wang , You-Xing Yang . Route for Turning Waste CH₄ and CO₂ into Valuable Products: Reforming for Syngas. University Chemistry, 2026, 41(2): 197-207. doi: 10.12461/PKU.DXHX202503012
13. [13]
  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
14. [14]
  Feifei Yang , Wei Zhou , Chaoran Yang , Tianyu Zhang , Yanqiang Huang . Enhanced Methanol Selectivity in CO₂ Hydrogenation by Decoration of K on MoS₂ Catalyst. Acta Physico-Chimica Sinica, 2024, 40(7): 2308017-0. doi: 10.3866/PKU.WHXB202308017
15. [15]
  Jingkun Yu , Xue Yong , Ang Cao , Siyu Lu . Bi-Layer Single Atom Catalysts Boosted Nitrate-to-Ammonia Electroreduction with High Activity and Selectivity. Acta Physico-Chimica Sinica, 2024, 40(6): 2307015-0. doi: 10.3866/PKU.WHXB202307015
16. [16]
  Xinyu Xu , Jiale Lu , Bo Su , Jiayi Chen , Xiong Chen , Sibo Wang . Steering charge dynamics and surface reactivity for photocatalytic selective methane oxidation to ethane over Au/Ti-CeO₂. Acta Physico-Chimica Sinica, 2025, 41(11): 100153-0. doi: 10.1016/j.actphy.2025.100153
17. [17]
  Hailang JIA , Pengcheng JI , Hongcheng LI . Preparation and performance of nickel doped ruthenium dioxide electrocatalyst for oxygen evolution. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1632-1640. doi: 10.11862/CJIC.20240398
18. [18]
  Haiqiang Lin , Weizheng Weng , Jingdong Lin , Mingshu Chen , Xueming Fang , Lefu Yang . Diverse Variables-Driven Catalytic Optimization: Experimental Enhancement and Instructional Design for Selective Methane Oxidation on Supported Nickel-based Catalysts. University Chemistry, 2025, 40(11): 327-336. doi: 10.12461/PKU.DXHX202505106
19. [19]
  Yu Wang , Haiyang Shi , Zihan Chen , Feng Chen , Ping Wang , Xuefei Wang . 具有富电子Pt^δ−壳层的空心AgPt@Pt核壳催化剂：提升光催化H₂O₂生成选择性与活性. Acta Physico-Chimica Sinica, 2025, 41(7): 100081-0. doi: 10.1016/j.actphy.2025.100081
20. [20]
  Shihui Shi , Haoyu Li , Shaojie Han , Yifan Yao , Siqi Liu . Regioselectively Synthesis of Halogenated Arenes via Self-Assembly and Synergistic Catalysis Strategy. University Chemistry, 2024, 39(5): 336-344. doi: 10.3866/PKU.DXHX202312002

Get Citation

PDF

XML

Metrics

PDF Downloads(74)
Abstract views(6011)
HTML views(1504)

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