Citation: Mao Yu, Tian Shaixiao, Zhang Wei, Xu Guangyu. Preparation and Application of Vinamidinium Salts in Organic Synthesis[J]. Chinese Journal of Organic Chemistry, ;2016, 36(4): 700-710. doi: 10.6023/cjoc201511008 shu

Preparation and Application of Vinamidinium Salts in Organic Synthesis

  • Corresponding author: Xu Guangyu, 
  • Received Date: 3 November 2015
    Available Online: 2 December 2015

    Fund Project: 湖南省医药卫生科研计划课题(No.B2013-050)资助项目. (No.B2013-050)

  • As a kind of important three-carbon building block, vinamidinium salts have been widely used in organic synthesis. In this paper the synthetic methods of vinamidinium salts are summarized, and its applications in the synthesis of aldehydes, aromatic and heterocyclic compounds in recent years are reviewed.
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    1. [1]

      [1] Nair, V.; Cooper, C. S. J. Org. Chem. 1981, 46, 4759.

    2. [2]

      [2] Lloyd, D.; Hamish, M. Angew. Chem., Int. Ed. 1976, 15, 459.

    3. [3]

      [3] Coverdale, H. A.; Hsung, R. P. Chemtracts 2003, 16, 238.

    4. [4]

      [4] Arnold, Z. Coll. Czech. Chem. Commun. 1965, 30, 2125.

    5. [5]

      [5] Davies, I. W.; Marcoux, J-F.; Wu, J.; Palucki, M.; Corley, E. G.; Robbins, M. A.; Tsou, N.; Ball, R. G.; Dormer, P.; Larsen, R. D.; Reider, P. J. J. Org. Chem. 2000, 65, 4571.

    6. [6]

      [6] Davies, I. W.; Marcoux, J.-F.; Wu, J.; Dormer, P. G.; Hughes, D.; Reider, P. J. J. Org. Chem. 2001, 66, 251.

    7. [7]

      [7] Davies, I. W.; Tellers, D. M.; Shultz, S.; Fleitz, F. J.; Cai, D. W.; Sun, Y. K. Org. Lett. 2002, 4, 2969.

    8. [8]

      [8] Davies, I. W.; Marcoux, J.-F.; Taylor, J. Org. Synth. 2003, 80, 200.

    9. [9]

      [9] Selvi, S.; Perumal, P. T. Tetrahedron Lett. 1997, 38, 6263.

    10. [10]

      [10] Gupton, J. T.; Krumpe, K. E.; Burnham, B. S.; Dwornik, K. A.; Petrich, S. A.; Du, K. X.; Bruce, M. A.; Vu, P.; Vargas, M.; Keertikar, K. M.; Hosein, K. N.; Jones, C. R.; Sikorski, J. A. Tetrahedron 1998, 54, 5075.

    11. [11]

      [11] Wang, X.; Gao, J.; Weng, Y. Zhejiang Chem. Ind. 2012, 43, 14 (in Chinese). (汪霞, 高洁婷, 翁意意, 浙江化工, 2012, 43, 14.)

    12. [12]

      [12] Král, V.; Dvořák, D. Tetrahedron Lett. 1982, 23, 1725.

    13. [13]

      [13] Arnold, Z.; Buděšinský, M. J. Org. Chem. 1988, 53, 5352.

    14. [14]

      [14] Gupton, J. T.; Norman, B.; Wysong, E. Synth. Commun. 1985, 15, 1305.

    15. [15]

      [15] Gupton, J. T.; Riesinger, S. W.; Shah, A. S.; Gall, J. E.; Bevirt, K. M. J. Org. Chem. 1991, 56, 976.

    16. [16]

      [16] Yamanaka, H.; Hisaki, K.; Kase, K.; Ishihara, T. Tetrahedron Lett. 1998, 39, 4355.

    17. [17]

      [17] Davies, I. W.; Marcoux, J.-F.; Taylor, J. D. O.; Dormer, P. G.; Deeth, R. J.; Marcotte, F.-A.; Hughes, D. L.; Reider. P. J. Org. Lett. 2002, 4, 439.

    18. [18]

      [18] Davies, I. W.; Marcoux, J.-F.; Taylor, J. D. O.; Dormer, P. G.; Deeth, R. J.; Marcotte, F.-A.; Hughes, D. L.; Reider. P. J. J. Org. Chem.2004, 69, 1298.

    19. [19]

      [19] Jutz, V. C.; Wagner, R. M. Angew. Chem., Int. Ed. 1972, 84, 2992.

    20. [20]

      [20] Anderson, Jr., A. G.; Daugs, E. D.; Kao, L. G.; Wang, J.-F. J. Org. Chem. 1986, 51, 2961.

    21. [21]

      [21] Church, R.; Trust, R.; Albright, J. D.; Powell, D. W. J. Org. Chem. 1995, 60, 3750.

    22. [22]

      [22] Marcoux, J.-F.; Corley, E. G.; Rossen, K.; Pye, P.; Wu, J.; Robbins, M. A.; Davies, I. W.; Larsen, R. D.; Reider, P. J. J. Org. Lett. 2000, 2, 2339.

    23. [23]

      [23] Marcoux, J.-F.; Marcotte, F.-A.; Wu, J.; Dormer, P. G.; Davies, I. W.; Hughes, D.; Reider, P. J. J. Org. Chem.2001, 66, 4194.

    24. [24]

      [24] Guo, H.; Kang, C.; Qiu, X.; Jin, R.; Gao, L. Chin. J. Appl. Chem. 2005, 22, 462 (in Chinese). (郭海泉, 康传清, 邱雪鹏, 金日哲, 高连勋, 应用化学, 2005, 22, 462.)

    25. [25]

      [25] Wypych, J.-C.; Nguyen, T. M.; Bénéchie, M.; Marazano, C. J. Org. Chem. 2008, 73, 1169.

    26. [26]

      [26] Cho, I. S.; Gong, L. Y.; Muchowski, J. M. J. Org. Chem. 1991, 56, 7288.

    27. [27]

      [27] Zhang, X. H.; Zhong, W.; Li, X. Z.; Li, S. Chin. Chem. Lett. 2009, 20, 771.

    28. [28]

      [28] Shi, X. F.; Ishihara, T.; Yamanaka, H. Tetrahedron Lett. 1995, 36, 1527.

    29. [29]

      [29] Yamanaka, H.; Takekawa, T.; Morita, K.; Ishihara, T. Tetrahedron Lett. 1996, 37, 1829.

    30. [30]

      [30] Frutos, R. P.; Wei, X. D.; Patel, N. D.; Tampone, T. G.; Mulder, J. A.; Busacca, C. A.; Senanayake, C. H. J. Org. Chem. 2013, 78, 5800.

    31. [31]

      [31] Gupton, J. T.; Miller, R. B.; Krumpe, K. E.; Clough, S. C.; Banner, E. J.; Kanters, R. P. F.; Du, K. X.; Keertikar, K. M.; Lauerman, N. E.; Solano, J. M.; Adams, B. R.; Callahan, D. W.; Little, B. A.; Scharf, A. B.; Sikorski, J. A. Tetrahedron 2005, 61, 1845.

    32. [32]

      [32] Gupton, J. T.; Krolikowski, D. A.; Yu, R. H.; Riesinger, S. W. J. Org. Chem. 1990, 55, 4735.

    33. [33]

      [33] Smith, S. Q.; Dudek, S. T.; He, S. H.; Girod, J. A.; Nunes, S. R. Tetrahedron Lett. 2013, 54, 3965.

    34. [34]

      [34] Clemens, R. T.; Smith, S. Q. Tetrahedron Lett. 2005, 46, 1319.

    35. [35]

      [35] Yamanaka, H.; Takekawa, T.; Morita, K.; Ishihara, T. Tetrahedron Lett. 1996, 37, 1829.

    36. [36]

      [36] Gupton, J. T.; Wilkinson, D. R.; Sikorski, J. A.; Clough, S. C.; Miller, R. B.; Norwood, B. K. H.; Chertudi, I. B.; Hickenboth, C. R.; Cutro, S. R.; Petrich, S. A.; Hicks, F. A. Tetrahedron 2002, 58, 5467.

    37. [37]

      [37] Gupton, J. T.; Telang, N.; Gazzo, D. F.; Barelli, P. J.; Lescalleet, K. E.; Fagan, J. W.; Mills, B. J.; Finzel, K. L.; Kanters, R. P. F.; Crocker, K. R.; Dudek, S. T.; Lariviere, C. M.; Smith, S. Q.; Keertikar, K. M. Tetrahedron 2013, 69, 5829.

    38. [38]

      [38] Petrich, S. A.; Qian, Z. R.; Santiago, L. Y.; Gupton, J. T.; Sikorski, J. A. Tetrahedron 1994, 50, 12113.

    39. [39]

      [39] Angus. R. O.; Bryce, M. R.; Keshavarz-K, M.; Wudl, F. Synthesis 1988, 746.

    40. [40]

      [40] Mehranpour, A. M.; Hashemnia, S.; Shayan, Z. Synth. Commun. 2011, 41, 3501.

    41. [41]

      [41] Quast, H.; Seidenspinner, H.-M.; Stawitz, J. W. Eur. J. Org. Chem. 2013, 4852.

    42. [42]

      [42] Mehranpour, A. M.; Hashemnia, S.; Bashiri, E. Synth. Commun. 2013, 43, 1931.

    43. [43]

      [43] Mehranpour, A. M. Tetrahedron Lett. 2014, 55, 5229.

    44. [44]

      [44] Zhou, S.; Larios, E. S.; Gravel, M. J. Org. Chem. 2012, 77, 3576.

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