Citation: Li Zhen, Duan Weiliang. Recent Advances in the Asymmetric Conjugate Addition Reactions of Phosphorus Nucleophiles to Electron-Deficient Alkenes[J]. Chinese Journal of Organic Chemistry, ;2016, 36(8): 1805-1813. doi: 10.6023/cjoc201602018 shu

Recent Advances in the Asymmetric Conjugate Addition Reactions of Phosphorus Nucleophiles to Electron-Deficient Alkenes

  • Corresponding author: Duan Weiliang, wlduan@mail.sioc.ac.cn
  • Received Date: 19 February 2016
    Revised Date: 20 April 2016

    Fund Project: Project supported by the National Natural Science Foundation of China Nos. 20902099,21172238,21472218

Figures(15)

  • Chiral phosphines are very useful in the fields of asymmetric catalysis, pharmaceutical chemistry, and materials. These compounds have been used as ligands coordinated to transition metals or organocatalysts in various reactions to furnish optically active products with high efficiency. Asymmetric phosphorus-addition reaction can be utilized for the direct preparation of chiral phosphorus compounds. This review summarizes the recent progress in the field of enantioselective phosphorus-addition reactions. Several examples of transition metal- and organocatalyst-promoted asymmetric hydrophosphination reactions of electron-deficient alkenes have been introduced.
  • 加载中
    1. [1]

    2. [2]

      Kovacik, I.; Wicht, D. K.; Grewal, N. S.; Glueck, D. S.; Incarvito, C. D.; Guzei, I. A.; Rheingold, A. L. Organometallics 2000, 19, 950.(b) Scriban, C.; Kovacik, I.; Glueck, D. S. Organometallics 2005, 24, 4871. 

    3. [3]

    4. [4]

    5. [5]

      Sadow, A. D.; Haller, I.; Fadini, L.; Togni, A. J. Am. Chem. Soc. 2004, 126, 14704.(b) Sadow, A. D.; Togni, A. J. Am. Chem. Soc. 2005, 127, 17012. 

    6. [6]

      Bartoli, G.; Bosco, M.; Carlone, A.; Locatelli, M.; Mazzanti, A.; Sambri, L.; Melchiorre, P. Chem. Commun. 2007, 722.

    7. [7]

      Carlone, A.; Bartoli, G.; Bosco, M.; Sambri, L.; Melchiorre, P. Angew. Chem., Int. Ed. 2007, 46, 4504.(b) Ibrahem, I.; Rios, R.; Vesely, J.; Hammar, P.; Eriksson, L.; Himo, F.; Cordova, A. Angew. Chem., Int. Ed. 2007, 46, 4507.(c) Ibrahem, I.; Hammar, P.; Vesely, J.; Rios, R.; Eriksson, L.; Cordova, A. Adv. Synth. Catal. 2008, 350, 1875. 

    8. [8]

      Feng, J.-J.; Chen, X.-F.; Shi, M.; Duan, W.-L. J. Am. Chem. Soc. 2010, 132, 5562.

    9. [9]

       

    10. [10]

      Du, D.; Duan, W.-L. Chem. Commun. 2011, 47, 11101.(b) Chen, Y.-R.; Duan, W.-L. Org. Lett. 2011, 13, 5824.(c) Feng, J.-J.; Huang, M.; Lin, Z.-Q.; Duan, W.-L. Adv. Synth. Catal. 2012, 354, 3122.(d) Du, D.; Lin, Z.-Q.; Lu, J.-Z.; Li, C.; Duan, W.-L. Asian J. Org. Chem. 2013, 2, 392.(e) Lu, J.; Ye, J.; Duan, W.-L. Org. Lett. 2013, 15, 5016.(f) Huang, M.; Li, C.; Duan, W.-L.; Xu, S. Chem. Commun. 2012, 48, 11148.

    11. [11]

      Huang, Y.; Pullarkat, S. A.; Li, L.; Leung, P.-H. Chem. Commun. 2010, 6950.

    12. [12]

      Huang, Y.; Chew, R. J.; Li, Y.; Pullarkat, S. A.; Leung, P.-H. Org. Lett. 2011, 13. 5862.(b) Huang, Y.; Pullarkat, S. A.; Teong, S.; Chew, R. J.; Li, Y.; Leung, P.-H. Organometallics 2012, 31, 4871.(c) Chew, R. J.; Huang, Y.; Li, Y.; Pullarkat, S. A.; Leung, P.-H. Adv. Synth. Catal. 2013, 355, 1403.(d) Chew, R. J.; Teo, K. Y.; Huang, Y.; Li, B.-B.; Li, Y.; Pullarkat, S. A.; Leung, P.-H. Chem. Commun. 2014, 50, 8768.(e) Chew, R. J.; Lu, Y.; Jia, Y.-X.; Li, B.-B.; Wong, E. H. Y.; Goh, R.; Li, Y.; Huang, Y.; Pullarkat, S. A.; Leung, P.-H. Chem.-Eur. J. 2014, 20, 14514.(f) Chew, R. J.; Sepp, K.; Li, B.-B.; Li, Y.; Zhu, P.-C.; Tan, N. S.; Leung, P.-H. Adv. Synth. Catal. 2015, 357, 3297.

    13. [13]

      Yang, X.-Y.; Tay, W. S.; Li, Y.; Pullarkat, S. A.; Leung, P.-H. Organometallics 2015, 34, 5196.(b) Yang, X.-Y.; Tay, W.; Li, Y.; Pullarkat, S.; Leung, P.-H. Chem. Commun. 2016, 52, 4211. 

    14. [14]

      Yang, M.-J.; Liu, Y.-J.; Gong, J.-F.; Song, M.-P. Organometallics 2011, 30, 3793.(b) Hao, X.-Q.; Zhao, Y.-W.; Yang, J.-J.; Niu, J.-L.; Gong, J.-F.; Song, M.-P. Organometallics 2014, 33, 1801.(c) Hao, X. Q.; Huang, J. J.; Wang, T.; Lv, J.; Gong, J. F.; Song, M. P. J. Org. Chem. 2014, 79, 9512.

    15. [15]

      Ding, B.; Zhang, Z.; Xu, Y.; Liu, Y.; Sugiya, M.; Imamoto, T.; Zhang, W. Org. Lett. 2013, 15, 5476.(b) Xu, Y.; Yang, Z.; Ding, B.; Liu, D.; Liu, Y.; Sugiya, M.; Imamoto, T.; Zhang, W. Tetrahedron 2015, 71, 6832.

    16. [16]

      For reviews on asymmetric 1,6-addition reactions, see:(a) Csákÿ, A. G.; la Herran, G. de.; Murcia, M. C. Chem. Soc. Rev. 2010, 39, 4080.(b) Biju, A. T. ChemCatChem 2011, 3, 1847.(c) Silva, E. M. P.; Silva, A. M. S. Synthesis 2012, 44, 3109.

    17. [17]

      Lu, J.; Ye, J.; Duan, W.-L. Chem. Commun. 2014, 50, 698.(b) Huang, J.; Zhao, M.-X.; Duan, W.-L. Tetrahedron Lett. 2014, 55, 629.

    18. [18]

      Huang, Y.; Pullarkat, S. A.; Li, Y.; Leung, P.-H. Inorg. Chem. 2012, 51, 2533.

    19. [19]

      Li, C.; Li, W.-X.; Xu, S.; Duan, W.-L. Org. Chem. Front. 2014, 1, 541.

    20. [20]

      Chen, Y.-R.; Feng, J.-J.; Duan, W.-L. Tetrahedron Lett. 2014, 55, 595.

    21. [21]

      Fu, X.; Jiang, Z.; Tan, C.-H. Chem. Commun. 2007, 5058.

    22. [22]

      Zhao, D.; Yuan, Y.; Chan, Albert S. C.; Wang, R. Chem.-Eur. J. 2009, 15, 2738.(b) Zhao, D.; Wang, Y.; Mao, L.; Wang. R. Chem.-Eur. J. 2009, 15, 10983.(c) Zhao, D.; Mao, L.; Wang, Y.; Yang, D.; Zhang, Q.; Wang, R. Org. Lett. 2010, 12, 1880.(d) Zhao, D.; Mao, L.; Yang, D.; Wang, R. J. Org. Chem. 2010, 75, 6756.(e) Zhao, D.; Mao, L.; Wang, L.; Yang, D.; Wang. R. Chem. Commun. 2012, 48, 889.(f) Zhao, D.; Wang, L.; Yang, D.; Zhang, Y.; Wang. R. Chem.-Eur. J. 2012, 7, 881. 

    23. [23]

      Wen, S.; Li, L.; Wu, H.; Yu, F.; Liang, X.; Ye, J. Chem. Commun. 2010, 4806.

    24. [24]

      Russo, A.; Lattanzi, A. Eur. J. Org. Chem. 2010, 6736.

    25. [25]

      Luo, X.; Zhou, Z.; Li, X.; Liang, X.; Ye, J. RSC Adv. 2011, 1, 698.

    26. [26]

      Hatano, M.; Horibe, T.; Ishihara, K. Angew. Chem., Int. Ed. 2013, 52, 4549. 

    27. [27]

      Geng, Z-C.; Zhang, J.-X.; Li, N.; Chen, J.; Huang, X.-F.; Zhang, S.-Y.; Li, H.-Y.; Tao, J.-C.; Wang, X.-W. Tetrahedron 2014, 70, 417.

  • 加载中
    1. [1]

      Weina Wang Lixia Feng Fengyi Liu Wenliang Wang . Computational Chemistry Experiments in Facilitating the Study of Organic Reaction Mechanism: A Case Study of Electrophilic Addition of HCl to Asymmetric Alkenes. University Chemistry, 2025, 40(3): 206-214. doi: 10.12461/PKU.DXHX202407022

    2. [2]

      Ke QIAOYanlin LIShengli HUANGGuoyu 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

    3. [3]

      Xincan ZhouXueyao WangXiaokang ChenDi LanYuting GaoXiaoxia WangDaohao LiShuchao ZhangLijie ZhangGuanglei Wu . Charge redistribution on Pd mediated by electronically asymmetric carbon for boosting ethanol oxidation. Acta Physico-Chimica Sinica, 2026, 42(7): 100287-0. doi: 10.1016/j.actphy.2026.100287

    4. [4]

      Guilan He Yaofeng Yuan . 手性二茂铁双膦配体Xyliphos的合成及应用. University Chemistry, 2025, 40(8): 130-137. doi: 10.12461/PKU.DXHX202409122

    5. [5]

      Zihao Guo Shichen Ma Kin Shing Chan . 烯烃环化反应中6电子试剂的等瓣相似性和等电子关系. University Chemistry, 2025, 40(6): 160-166. doi: 10.12461/PKU.DXHX202408038

    6. [6]

      Qianwen HanTenglong ZhuQiuqiu LüMahong YuQin Zhong . Performance and Electrochemical Asymmetry Optimization of Hydrogen Electrode Supported Reversible Solid Oxide Cell. Acta Physico-Chimica Sinica, 2025, 41(1): 100005-0. doi: 10.3866/PKU.WHXB202309037

    7. [7]

      Xilin Zhao Xingyu Tu Zongxuan Li Rui Dong Bo Jiang Zhiwei Miao . Research Progress in Enantioselective Synthesis of Axial Chiral Compounds. University Chemistry, 2024, 39(11): 158-173. doi: 10.12461/PKU.DXHX202403106

    8. [8]

      Tianqi Sheng Xuenan Yang Zhaoyang Li Shaoguang Zhang . Understanding structural influences in organoelement compounds through configurational inversion of amines, phosphines, and sulfoxides. University Chemistry, 2026, 41(7): 415-429. doi: 10.12461/PKU.DXHX202505012

    9. [9]

      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

    10. [10]

      Qiwen Chen Baolei Wang . Research Progress on One-Electron σ-Bond of Organic Compounds. University Chemistry, 2025, 40(11): 191-198. doi: 10.12461/PKU.DXHX202412136

    11. [11]

      Xudong Liu Huili Fan Junping Xiao Min Yang Yan Li . Teaching Approaches to the AE + AN Mechanism of Electrophilic Addition Reactions between Olefins and Inorganic Acids in Organic Chemistry. University Chemistry, 2025, 40(7): 367-372. doi: 10.12461/PKU.DXHX202409041

    12. [12]

      Qi Zhang Ziyu Liu Hongxia Tan Jun Tong Dazhen Xu . Research Progress on Direct Synthesis of β-Hydroxy Sulfones via Difunctionalization of Olefins. University Chemistry, 2025, 40(11): 199-209. doi: 10.12461/PKU.DXHX202412064

    13. [13]

      Qi Liang Xinxin Wang Xinmiao Zhao Mohan Yu Yue Sun . 电子圆二色谱结合量子化学计算的氨基酸手性解析——介绍一个计算化学综合实验. University Chemistry, 2026, 41(5): 380-390. doi: 10.12461/PKU.DXHX202511096

    14. [14]

      Dan Liu . 可见光-有机小分子协同催化的不对称自由基反应研究进展. University Chemistry, 2025, 40(6): 118-128. doi: 10.12461/PKU.DXHX202408101

    15. [15]

      Dengke Ma . Application of Integrating Fundamental Knowledge and Cutting-Edge Developments in the Teaching of Organic Synthesis: Taking the Asymmetric Meinwald Rearrangement as an Example. University Chemistry, 2026, 41(4): 67-74. doi: 10.12461/PKU.DXHX202502112

    16. [16]

      Yan Li Xinze Wang Xue Yao Shouyun Yu . 基于激发态手性铜催化的烯烃EZ异构的动力学拆分——推荐一个本科生综合化学实验. University Chemistry, 2024, 39(5): 1-10. doi: 10.3866/PKU.DXHX202309053

    17. [17]

      Shaohua Wu Jianfeng Yan Chunfa Xu Yuanming Li Kai Yang Caixia Lin . Construction of the synthetic chemistry experiment course under the Chemistry “101 Plan”: instructional design and implementation of the L-proline-catalyzed asymmetric aldol condensation reaction experiment. University Chemistry, 2026, 41(6): 152-159. doi: 10.12461/PKU.DXHX202511100

    18. [18]

      Linjie ZHUXufeng LIU . Electrocatalytic hydrogen evolution performance of tetra-iron complexes with bridging diphosphine ligands. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 321-328. doi: 10.11862/CJIC.20240207

    19. [19]

      Dongheng WANGSi LIShuangquan ZANG . Construction of chiral alkynyl silver chains and modulation of chiral optical properties. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 131-140. doi: 10.11862/CJIC.20240379

    20. [20]

      Ruiying WANGHui WANGFenglan CHAIZhinan ZUOBenlai WU . Three-dimensional homochiral Eu(Ⅲ) coordination polymer and its amino acid configuration recognition. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 877-884. doi: 10.11862/CJIC.20250052

Metrics
  • PDF Downloads(0)
  • Abstract views(3485)
  • HTML views(837)

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