Citation: Zhu Xinju, Niu Junlong, Zhao Xuemei, Hao Xinqi, Song Maoping. Synthesis of Chiral Bis(imidazoline) Ligands with Biphenyl Backbone and Their Application in the Asymmetric Cyclopropanation Reaction[J]. Chinese Journal of Organic Chemistry, ;2018, 38(1): 118-123. doi: 10.6023/cjoc201708037 shu

Synthesis of Chiral Bis(imidazoline) Ligands with Biphenyl Backbone and Their Application in the Asymmetric Cyclopropanation Reaction

College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou 450001

Corresponding author: Hao Xinqi, xqhao@zzu.edu.cn Song Maoping, mpsong@zzu.edu.cn
Received Date: 19 August 2017
Revised Date: 8 November 2017
Available Online: 17 January 2017
Fund Project: the National Natural Science Foundation of Chin 21672192the National Natural Science Foundation of Chin 21528201the China Postdoctoral Science Foundation 2016M602254Project supported by the National Natural Science Foundation of China (Nos. 21528201, 21672192) and the China Postdoctoral Science Foundation (No. 2016M602254)

Figures(4)

A serial of biphenyl bisimidazolines containing both axial and central chirality have been synthesized for the first time. Compared with common method, Ullmann coupling methodology exhibited superior performance expecially for t-Bu substituted ligands. The obtained ligands were further applied in the Cu-catalyzed asymmetric cyclopropanation.
- imidazoline,
- axial chirality,
- central chirality,
- asymmetric cyclopropanation
1. [1]
  (a) Farina, V. ; Reeves, J. T. ; Senanayake, C. H. ; Song, J. J. Chem. Rev. 2006, 106, 2734.
  (b) Blaser, H. U. Adv. Synth. Catal. 2002, 344, 17.
2. [2]
  For review, see:(a) Rechavi, D.; Lemaire, M. Chem. Rev. 2002, 102, 3467.
  (b) McManus, H. A.; Guiry, P. J. Chem. Rev. 2004, 104, 4151.
  (c) Desimoni, G.; Faita, G.; J rgensen, K. A. Chem. Rev. 2006, 106, 3561.
  (d) Hargaden, G. C.; Guiry, P. J. Chem. Rev. 2009, 109, 2505.
  (e) Desimoni, G.; Faita, G.; J rgensen, K. A. Chem. Rev. 2011, 111, PR284.
3. [3]
  (a) Knowles, W. S.; Sabacky, M. J.; Vineyard, B. D.; Weinkauff, D. J. J. Am. Chem. Soc. 1975, 97, 2567.
  (b) Evans, D. A.; Faul, M. M.; Bilodeau, M. T.; Anderson, B. A.; Barnes, D. M. J. Am. Chem. Soc. 1993, 115, 5328.
4. [4]
  (a) Zhang, W. ; Hirao, T. ; Ikeda, I. Tetrahedron Lett. 1996, 37, 4545.
  (b) Schaarschmidt, D. ; Lang, H. Organometallics 2013, 32, 5668.
5. [5]
  (a) Nelson, T. D. ; Meyers, A. I. J. Org. Chem. 1994, 59, 2655.
  (b) Gant, T. G. ; Noe, M. C. ; Corey, E. J. Tetrahedron Lett. 1995, 36, 8745.
  (c) Meyers, A. I. ; McKennon, M. J. Tetrahedron Lett. 1995, 36, 5869.
6. [6]
  (a) Uozumi, Y. ; Kyota, H. ; Kishi, E. ; Kitayama, K. ; Hayashi, T. Tetrahedron: Asymmetry 1996, 7, 1603.
  (b) Andrus, M. B. ; Asgari, D. ; Sclafani, J. A. J. Org. Chem. 1997, 62, 9365.
  (c) Meyers, A. I. ; Price, A. J. Org. Chem. 1998, 63, 412.
  (d) Andrus, M. B. ; Asgari, D. Tetrahedron 2000, 56, 5775.
  (e) Khanbabaee, K. ; Basceken, S. ; Fl rke, U. Eur. J. Org. Chem. 2007, 831.
7. [7]
  (a) Imai, Y. ; Zhang, W. ; Kida, T. ; Nakatsuji, Y. ; Ikeda, I. Tetrahedron Lett. 1997, 38, 2681.
  (b) Imai, Y. ; Zhang, W. ; Kida, T. ; Nakatsuji, Y. ; Ikeda, I. J. Org. Chem. 2000, 65, 3326.
  (c) Gómez, M. ; Jansat, S. ; Muller, G. ; Maestro, M. A. ; Mahía, J. Organometallics 2002, 21, 1077.
  (d) Zhang, W. ; Xie, F. ; Matsuo, S. ; Imahori, Y. ; Kida, T. ; Nakatsuji, Y. ; Ikeda, I. Tetrahedron: Asymmetry 2006, 17, 767.
  (e) Zhang, Y. J. ; Wang, F. ; Zhang, W. J. Org. Chem. 2007, 72, 9208.
  (f) Wang, F. ; Zhang, Y. J. ; Wei, H. ; Zhang, J. ; Zhang, W. Tetrahedron Lett. 2007, 48, 4083.
  (g) Wang, F. ; Zhang, Y. J. ; Yang, G. ; Zhang, W. Tetrahedron Lett. 2007, 48, 4179.
  (h) Wang, F. ; Yang, G. ; Zhang, Y. J. ; Zhang, W. Tetrahedron 2008, 64, 9413.
  (i) Jiang, F. ; Wu, Z. ; Yang, G. ; Xie, F. ; Zhang, W. Tetrahedron Lett. 2011, 52, 2844.
  (j) Liu, Q. ; Wen, K. ; Zhang, Z. ; Wu, Z. ; Zhang, Y. J. ; Zhang, W. Tetrahedron 2012, 68, 5209.
  (k) Samadi, S. ; Jadidi, K. ; Notash, B. Tetrahedron: Asymmetry 2013, 24, 269.
8. [8]
  (a) Hsiao, Y. ; Hegedus, L. S. J. Org. Chem. 1997, 62, 3586.
  (b) Boland, N. A. ; Casey, M. ; Hynes, S. J. ; Matthews, J. W. ; Smyth, M. P. J. Org. Chem. 2002, 67, 3919.
  (c) Fujioka, H. ; Murai, K. ; Ohba, Y. ; Hiramatsu, A. ; Kita, Y. Tetrahedron Lett. 2005, 46, 2197.
  (d) Elders, N. ; Schmitz, B. F. ; de Kanter, F. J. J. ; Ruijter, E. ; Groen, M. B. ; Orru, R. V. A. J. Org. Chem. 2007, 72, 6135.
  (e) Liu, H. ; Du, D. -M. Adv. Synth. Catal. 2009, 351, 489.
9. [9]
  (a) Boland, N. A. ; Casey, M. ; Hynes, S. J. ; Matthews, J. W. ; Müller-Bunz, H. ; Wilkes, P. Org. Biomol. Chem. 2004, 2, 1995.
  (b) Nakamura, S. ; Hyodo, K. ; Nakamura, Y. ; Shibata, N. ; Toru, T. Adv. Synth. Catal. 2008, 350, 1443.
  (c) Takizawa, S. ; Hirata, S. ; Murai, K. ; Fujioka, H. ; Sasai, H. Org. Biomol. Chem. 2014, 12, 5827.
  (d) Hyodo, K. ; Nakamura, S. ; Shibata, N. Angew. Chem., Int. Ed. 2012, 51, 10337.
  (e) Arai, T. ; Moribatake, T. ; Masu, H. Chem. Eur. J. 2015, 21, 10671.
  (f) Kondo, M. ; Nishi, T. ; Hatanaka, T. ; Funahashi, Y. ; Nakamura, S. Angew. Chem., Int. Ed. 2015, 54, 8198.
  (g) Hellmuth, T. ; Frey, W. ; Peters, R. Angew. Chem., Int. Ed. 2015, 54, 2788.
10. [10]
  (a) Hao, X. -Q. ; Gong, J. -F. ; Du, C. -X. ; Wu, L. -Y. ; Wu, Y. -J. ; Song, M. -P. Tetrahedron Lett. 2006, 47, 5033.
  (b) Wu, L. -Y. ; Hao, X. -Q. ; Xu, Y. -X. ; Jia, M. -Q. ; Wang, Y. -N. ; Gong, J. -F. ; Song, M. -P. Organometallics 2009, 28, 3369.
  (c) Hao, X. -Q. ; Xu, Y. -X. ; Yang, M. -J. ; Wang, L. ; Niu, J. -L. ; Gong, J. -F. ; Song, M. -P. Organometallics 2012, 31, 835.
11. [11]
  Hao, X.-Q.; Zhao, Y.-W.; Yang, J.-J.; Niu, J.-L.; Gong, J.-F.; Song, M.-P. Organometallics 2014, 33, 1801. doi: 10.1021/om500144b
12. [12]
  Shao, D.-D.; Niu, J.-L.; Hao, X.-Q.; Gong, J.-F.; Song, M.-P. Dalton Trans. 2011, 40, 9012. doi: 10.1039/c1dt10329f
13. [13]
  (a) Wang, T. ; Hao, X. -Q. ; Huang, J. -J. ; Niu, J. -L. ; Gong, J. -F. ; Song, M. -P. J. Org. Chem. 2013, 78, 8712.
  (b) Wang, T. ; Niu, J. -L. ; Liu, S. -L. ; Huang, J. -J. ; Gong, J. -F. ; Song, M. -P. Adv. Synth. Catal. 2013, 355, 927.
14. [14]
  For reviews, please see: (a) Niu, J. -L. ; Hao, X. -Q. ; Gong, J. -F. ; Song, M. -P. Dalton Trans. 2011, 40, 5135.
  (b) Hao, X. -Q. ; Niu, J. -L. ; Zhao, X. -M. ; Gong, J. -F. ; Song, M. -P. Chin. J. Org. Chem. 2013, 33, 663(in Chinese).
15. [15]
  (a) Ullmann, F. ; Bielecki, J. Chem. Ber. 1901, 34, 2174.
  (b) Carlin, R. B. ; Swakon, E. A. J. Am. Chem. Soc. 1955, 77, 966.
16. [16]
  Hao, X.-Q.; Shen, M.-Z.; Jian, N.-G.; Pang, W.; Shen, X.-J.; Zhu, X.; Song, M.-P. Tetrahedron:Asymmetry 2016, 27, 163. doi: 10.1016/j.tetasy.2016.01.015
1. [1]
  Yiming Yang , Lichao Sun , Qingfeng Zhang . Plasmonic nanocrystals with intrinsic chirality: Biomolecule-directed synthesis and applications. Chinese Journal of Structural Chemistry, 2025, 44(1): 100467-100467. doi: 10.1016/j.cjsc.2024.100467
2. [2]
  Fengying Ye , Ming Hu , Jun Luo , Wei Yu , Zhirong Xu , Jinjin Fu , Yansong Zheng . Significantly boosting circularly polarized luminescence by synergy of helical and planar chirality. Chinese Chemical Letters, 2025, 36(5): 110724-. doi: 10.1016/j.cclet.2024.110724
3. [3]
  Long Jin , Jian Han , Dongmei Fang , Min Wang , Jian Liao . Pd-catalyzed asymmetric carbonyl alkynylation: Synthesis of axial chiral ynones. Chinese Chemical Letters, 2024, 35(6): 109212-. doi: 10.1016/j.cclet.2023.109212
4. [4]
  Qianyun Ye , Yuanyuan Liang , Yuhe Yuan , Xiaohuan Sun , Liqi Zhu , Xuan Wu , Jie Han , Rong Guo . pH-responsive chiral supramolecular cysteine-Zn²⁺-indocyanine green assemblies for triple-level chirality-specific anti-tumor efficacy. Chinese Chemical Letters, 2025, 36(5): 110432-. doi: 10.1016/j.cclet.2024.110432
5. [5]
  Yanan Zhou , Li Sheng , Lanlan Chen , Wenhua Zhang , Jinlong Yang . Axial coordinated iron-nitrogen-carbon as efficient electrocatalysts for hydrogen evolution and oxygen redox reactions. Chinese Chemical Letters, 2025, 36(1): 109588-. doi: 10.1016/j.cclet.2024.109588
6. [6]
  Ze Zhang , Lei Yang , Jin-Ru Liu , Hao Hu , Jian-Li Mi , Chao Su , Bei-Bei Xiao , Zhi-Min Ao . Improved oxygen electrocatalysis at FeN₄ and CoN₄ sites via construction of axial coordination. Chinese Chemical Letters, 2025, 36(2): 110013-. doi: 10.1016/j.cclet.2024.110013
7. [7]
  Pei Cao , Yilan Wang , Lejian Yu , Miao Wang , Liming Zhao , Xu Hou . Dynamic asymmetric mechanical responsive carbon nanotube fiber for ionic logic gate. Chinese Chemical Letters, 2024, 35(6): 109421-. doi: 10.1016/j.cclet.2023.109421
8. [8]
  Yanxin Jiang , Kwai Wun Cheng , Zhiping Yang , Jun (Joelle) Wang . Pd-catalyzed enantioselective and regioselective asymmetric hydrophosphorylation and hydrophosphinylation of enynes. Chinese Chemical Letters, 2025, 36(5): 110231-. doi: 10.1016/j.cclet.2024.110231
9. [9]
  Tengfei Xuan , Yuan Pan , Zhenyu Shi , Yang Wang . Organocatalytic asymmetric synthesis of oxazolines from N-acylimines. Chinese Chemical Letters, 2025, 36(6): 110352-. doi: 10.1016/j.cclet.2024.110352
10. [10]
  Xiaoxu Duan , Junli Xu , Jiwei Li , Congcong Du , Kai Chen , Teng Xu , Yifei Sun , Haifeng Xiong . Enhancing CO₂ reduction efficiency with axial oxygen coordinated Ni-N₄ active sites on hierarchical pore N-doped carbon. Chinese Chemical Letters, 2025, 36(7): 110340-. doi: 10.1016/j.cclet.2024.110340
11. [11]
  Zhen Liu , Zhi-Yuan Ren , Chen Yang , Xiangyi Shao , Li Chen , Xin Li . Asymmetric alkenylation reaction of benzoxazinones with diarylethylenes catalyzed by B(C₆F₅)₃/chiral phosphoric acid. Chinese Chemical Letters, 2024, 35(5): 108939-. doi: 10.1016/j.cclet.2023.108939
12. [12]
  Yu-Hang Miao , Zheng-Xu Zhang , Xu-Yi Huang , Yuan-Zhao Hua , Shi-Kun Jia , Xiao Xiao , Min-Can Wang , Li-Ping Xu , Guang-Jian Mei . Catalytic asymmetric dearomative azo-Diels–Alder reaction of 2-vinlyindoles. Chinese Chemical Letters, 2024, 35(4): 108830-. doi: 10.1016/j.cclet.2023.108830
13. [13]
  Chao Chen , Wenwen Yu , Guangen Huang , Xuelian Ren , Xiangli Chen , Yixin Li , Shenggui Liang , Mengmeng Xu , Mingyue Zheng , Yaxi Yang , He Huang , Wei Tang , Bing Zhou . Asymmetric macrocyclization enabled by Rh(Ⅲ)-catalyzed CH activation: Enantioenriched macrocyclic inhibitor of Zika virus infection. Chinese Chemical Letters, 2024, 35(11): 109574-. doi: 10.1016/j.cclet.2024.109574
14. [14]
  Xiang Huang , Dongzhen Xu , Yang Liu , Xia Huang , Yangfan Wu , Dongmei Fang , Bing Xia , Wei Jiao , Jian Liao , Min Wang . Asymmetric synthesis of difluorinated α-quaternary amino acids (DFAAs) via Cu-catalyzed difluorobenzylation of aldimine esters. Chinese Chemical Letters, 2024, 35(12): 109665-. doi: 10.1016/j.cclet.2024.109665
15. [15]
  Guang Xu , Cuiju Zhu , Xiang Li , Kexin Zhu , Hao Xu . Copper-catalyzed asymmetric [4+1] annulation of yne–allylic esters with pyrazolones. Chinese Chemical Letters, 2025, 36(4): 110114-. doi: 10.1016/j.cclet.2024.110114
16. [16]
  Jieshuai Xiao , Yuan Zheng , Yue Zhao , Zhuangzhi Shi , Minyan Wang . Asymmetric Nozaki-Hiyama-Kishi (NHK)-type reaction of isatins with aromatic iodides by cobalt catalysis. Chinese Chemical Letters, 2025, 36(5): 110243-. doi: 10.1016/j.cclet.2024.110243
17. [17]
  Ya-Ling Li , Jia-Wei Ke , Yue Liu , Dong-Mei Yao , Jing-Dong Zhang , You-Cai Xiao , Fen-Er Chen . Asymmetric conjugated addition of aryl Grignard reagents for the construction of chromanones bearing quaternary stereogenic centers in batch and flow. Chinese Chemical Letters, 2025, 36(6): 110377-. doi: 10.1016/j.cclet.2024.110377
18. [18]
  Fangqing Zhang , Yu Wang , Zhenda Tan , Yangbin Liu , Lijuan Song , Xiaoming Feng . Catalytic asymmetric inverse-electron-demand Diels–Alder reaction of 2-pyrones with aryl enol ethers. Chinese Chemical Letters, 2025, 36(7): 110581-. doi: 10.1016/j.cclet.2024.110581
19. [19]
  Ruixue Liu , Xiaobing Ding , Qiwei Lang , Gen-Qiang Chen , Xumu Zhang . Enantioselective and divergent construction of chiral amino alcohols and oxazolidin-2-ones via Ir-f-phamidol-catalyzed dynamic kinetic asymmetric hydrogenation. Chinese Chemical Letters, 2025, 36(3): 110037-. doi: 10.1016/j.cclet.2024.110037
20. [20]
  Tiancong Shi , Xi Chen , Xiao Zhou , Hongyi Zhang , Fuping Han , Lihan Cai , Wen Sun , Jianjun Du , Jiangli Fan , Xiaojun Peng . Azaindole-based asymmetric pentamethine cyanine dye for mitochondrial pH detection and near-infrared ratiometric fluorescence imaging of mitophagy. Chinese Chemical Letters, 2025, 36(6): 110408-. doi: 10.1016/j.cclet.2024.110408

Get Citation

PDF

XML

Metrics

PDF Downloads(10)
Abstract views(2456)
HTML views(128)

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