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

  • 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.
  • 加载中
    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

  • 加载中
    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 YeMing HuJun LuoWei YuZhirong XuJinjin FuYansong 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 JinJian HanDongmei FangMin WangJian 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 YeYuanyuan LiangYuhe YuanXiaohuan SunLiqi ZhuXuan WuJie HanRong 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 ZhouLi ShengLanlan ChenWenhua ZhangJinlong 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 ZhangLei YangJin-Ru LiuHao HuJian-Li MiChao SuBei-Bei XiaoZhi-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 CaoYilan WangLejian YuMiao WangLiming ZhaoXu 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 JiangKwai Wun ChengZhiping YangJun (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 XuanYuan PanZhenyu ShiYang 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]

      Zhen LiuZhi-Yuan RenChen YangXiangyi ShaoLi ChenXin 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

    11. [11]

      Yu-Hang MiaoZheng-Xu ZhangXu-Yi HuangYuan-Zhao HuaShi-Kun JiaXiao XiaoMin-Can WangLi-Ping XuGuang-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

    12. [12]

      Chao ChenWenwen YuGuangen HuangXuelian RenXiangli ChenYixin LiShenggui LiangMengmeng XuMingyue ZhengYaxi YangHe HuangWei TangBing 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

    13. [13]

      Xiang HuangDongzhen XuYang LiuXia HuangYangfan WuDongmei FangBing XiaWei JiaoJian LiaoMin 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

    14. [14]

      Guang XuCuiju ZhuXiang LiKexin ZhuHao 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

    15. [15]

      Jieshuai XiaoYuan ZhengYue ZhaoZhuangzhi ShiMinyan 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

    16. [16]

      Ya-Ling LiJia-Wei KeYue LiuDong-Mei YaoJing-Dong ZhangYou-Cai XiaoFen-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

    17. [17]

      Ruixue LiuXiaobing DingQiwei LangGen-Qiang ChenXumu 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

    18. [18]

      Tiancong ShiXi ChenXiao ZhouHongyi ZhangFuping HanLihan CaiWen SunJianjun DuJiangli FanXiaojun 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

    19. [19]

      Zhirong YangShan WangMing JiangGengchen LiLong LiFangzhi PengZhihui Shao . One stone three birds: Ni-catalyzed asymmetric allenylic substitution of allenic ethers, hydroalkylation of 1,3-enynes and double alkylation of enynyl ethers. Chinese Chemical Letters, 2024, 35(8): 109518-. doi: 10.1016/j.cclet.2024.109518

    20. [20]

      Xiaohui FuYanping ZhangJuan LiaoZhen-Hua WangYong YouJian-Qiang ZhaoMingqiang ZhouWei-Cheng Yuan . Palladium-catalyzed enantioselective decarboxylation of vinyl cyclic carbamates: Generation of amide-based aza-1,3-dipoles and application to asymmetric 1,3-dipolar cycloaddition. Chinese Chemical Letters, 2024, 35(12): 109688-. doi: 10.1016/j.cclet.2024.109688

Metrics
  • PDF Downloads(9)
  • Abstract views(2427)
  • HTML views(126)

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

  1. 本站搜索
  2. 百度学术搜索
  3. 万方数据库搜索
  4. CNKI搜索
Address:Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888
Powered By info@rhhz.net

/

DownLoad:  Full-Size Img  PowerPoint
Return