Enyne Metathesis

  • Miwako Mori
Chapter
Part of the Topics in Organometallic Chemistry book series (TOPORGAN, volume 1)

Abstract

Enyne metathesis is unique and interesting in synthetic organic chemistry. Since it is difficult to control intermolecular enyne metathesis, this reaction is used as intramolecular enyne metathesis. There are two types of enyne metathesis: one is caused by [2+2] cycloaddition of a multiple bond and transition metal carbene complex, and the other is an oxidative cyclization reaction caused by low-valent transition metals. In these cases, the alkylidene part migrates from alkene to alkyne carbon. Thus, this reaction is called an alkylidene migration reaction or a skeletal reorganization reaction. Many cyclized products having a diene moiety were obtained using intramolecular enyne metathesis. Very recently, intermolecular enyne metathesis has been developed between alkyne and ethylene as novel diene synthesis.

Keywords

Enyne metathesis Enyne Metathesis Carbene complex [2+2] Cycloaddition 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1. (a)
    Martin SF, Liao Y, Rein T (1994) Tetrahedron Lett 35:691.CrossRefGoogle Scholar
  2. 1. (b)
    Borer BC, Deerenberg S, Bieräugel H, Pandit UK (1994) Tetrahedron Lett 35:3191.CrossRefGoogle Scholar
  3. 1. (c)
    Martin SF, Wagman AS (1995) Tetrahedron Lett 36:1169.CrossRefGoogle Scholar
  4. 1. (d)
    Houri AF, Xu Z, Cogan D, Hoveyda AH (1995) J Am Chem Soc 117:2943.CrossRefGoogle Scholar
  5. 1. (e)
    Xu Z, Johannes CW, Salman SS, Hoveyda AH (1996) J Am Chem Soc 118:10926.CrossRefGoogle Scholar
  6. 1. (f)
    Fürstner A, Langemann K (1996) J Org Chem 61:8746.CrossRefGoogle Scholar
  7. 1. (g)
    Nicolaou KC, He Y, Vourloumis D, Vallberg H, Yang Z (1996) Angew Chem Int Ed Engl 35:2399.CrossRefGoogle Scholar
  8. 1. (h)
    Barrett AGM, Baugh SPD, Gibson VC, Giles MR, Marshall EL, Procopiou PA (1997) J Chem Soc Chem Commun 155.Google Scholar
  9. 1. (i)
    Meng D, Su D-S, Balog A, Bertinato P, Sorensen EJ, Danishefsky SJ, Zheng Y-H, Chou T-C, He L, Horwitz SB (1997) J Am Chem Soc 119:2733.CrossRefGoogle Scholar
  10. 1. (j)
    Clark JS, Kettle JG (1997) Tetrahedron Lett 38:127.CrossRefGoogle Scholar
  11. 1. (k)
    Fürstner A, Kindler N (1996) Tetrahedron Lett 37:7005.CrossRefGoogle Scholar
  12. 1. (l)
    Fürstner A, Langemann K (1996) J Org Chem 61:3942.CrossRefGoogle Scholar
  13. 1. (m)
    Fürstner A, Langemann K (1997) Synthesis 792.Google Scholar
  14. 1. (n)
    Fürstner A, Müller T (1997) Synlett 1010.Google Scholar
  15. 1. (o)
    Chang S, Grubbs RH (1997) Tetrahedron Lett 38:4757.CrossRefGoogle Scholar
  16. 1. (p)
    Delgado M, Martin JD (1997) Tetrahedron Lett 38:6299.CrossRefGoogle Scholar
  17. 1. (q)
    Linderman RJ, Siedlecki J, O’Neill SA, Sun H (1997) J Am Chem Soc 119:6919.CrossRefGoogle Scholar
  18. 1. (r)
    Garro-Hélion F, Guibé F (1996) J Chem Soc Chem Commun 641Google Scholar
  19. 2. (a)
    Nguyen ST, Johnson LK, Grubbs RH, Ziller JW (1992) J Am Chem Soc 114:3974.CrossRefGoogle Scholar
  20. 2. (b)
    Nguyen ST, Grubbs RH, Ziller JW (1993) J Am Chem Soc 115:9858CrossRefGoogle Scholar
  21. 3.
    Schrock RR, Murdzek JS, Bazan GC, Robbins J, DiMare M, O’Regan M (1990) J Am Chem Soc 112:3875CrossRefGoogle Scholar
  22. 4.
    Recently, some elegant intermolecular olefin-metatheses were reported. (a) Crowe WE, Zhang ZJ (1993) J Am Chem Soc 115:10998.CrossRefGoogle Scholar
  23. 4. (b)
    Crowe WE, Goldberg DR, Zhang ZJ (1996) Tetrahedron Lett 37:2117.CrossRefGoogle Scholar
  24. 4. (c)
    Crowe WE, Goldberg DR ( 1995) J Am Chem Soc 117:5162.CrossRefGoogle Scholar
  25. 4. (d)
    Barrett AGM, Beall JC, Gibson VC, Giles MR, Walker GLP ( 1996) J Chem Soc Chem Comm 2229.Google Scholar
  26. 4. (e)
    Barrett AGM, Baugh SPD, Gibson VC, Giles MR, Marshall EL, Procopiou PA (1994) J Chem Soc Chem Commun 2505.Google Scholar
  27. 4. (f)
    Schuster M, Pemerstorfer J, Blechert S (1996) Angew Chem Int Ed Engl 35:1979.CrossRefGoogle Scholar
  28. 4. (g)
    Feng J, Schuster M, Blechert S (1997) Synlett 129.Google Scholar
  29. 4. (h)
    Gibson SF, Gibson VC, Keen SP (1997) J Chem Soc Chem Commun 1107.Google Scholar
  30. 4. (i)
    Snapper ML, Tallarico JA, Randall ML (1997) J Am Chem Soc 119:1478.CrossRefGoogle Scholar
  31. 4. (j)
    Tallarico JA, Bonitatebus Jr. PJ, Snapper ML (1997) J Am Chem Soc 119:7157CrossRefGoogle Scholar
  32. 5. (a)
    Fu GC, Grubbs RH (1992) J Am Chem Soc 114:5426.CrossRefGoogle Scholar
  33. 5. (b)
    Fu GC, Grubbs RH (1992) J Am Chem Soc 114:7324.CrossRefGoogle Scholar
  34. 5. (c)
    Fu GC, Grubbs RH (1993) J Am Chem Soc 115:3800.CrossRefGoogle Scholar
  35. 5. (d)
    Fu GC, Nguyen ST, Grubbs RH (1993) J Am Chem Soc 115:9856.CrossRefGoogle Scholar
  36. 5. (e)
    Fujimura O, Fu GC, Grubbs RH (1994) J Org Chem 59:4029.CrossRefGoogle Scholar
  37. 5. (f)
    Grubbs RH, Miller SJ, Fu GC (1995) Acc Chem Res 28:446.CrossRefGoogle Scholar
  38. 5. (g)
    Miller SJ, Grubbs RH (1995) J Am Chem Soc 117:5855.CrossRefGoogle Scholar
  39. 5. (h)
    Leconte M, Jourdan I, Pagano S, Lefebvre F, Basset J-M (1995) J Chem Soc Chem Commun 857.Google Scholar
  40. 5. (i)
    Shon Y-S, Lee TR (1997) Tetrahedron Lett 38:1283.CrossRefGoogle Scholar
  41. 5. (j)
    Armstrong SK, Christie BA (1996) Tetrahedron Lett 37:9373CrossRefGoogle Scholar
  42. 6. (a)
    Katz TJ, Sivavec TM (1985) J Am Chem Soc 107:737.CrossRefGoogle Scholar
  43. 6. (b)
    Sivavec TM, Katz TJ (1989) Organometallics 8:1620CrossRefGoogle Scholar
  44. 7. (a)
    Hoye TR, Suriano JA (1992) Organometallics 11:2044.CrossRefGoogle Scholar
  45. 7. (b)
    Korkowski PF, Hoye TR, Rydberg DB (1988) J Am Chem Soc 110:2676CrossRefGoogle Scholar
  46. 8. (a)
    Mori M, Watanuki S (1992) J Chem Soc Chem Commun 1082.Google Scholar
  47. 8. (b)
    Mori M, Watanuki S (1993) Heterocycles 35:679.CrossRefGoogle Scholar
  48. 8. (c)
    Watanuki S, Mori M (1995) Organometallics 14:5054CrossRefGoogle Scholar
  49. 9. (a)
    Watanuki S, Ochifuji N, Mori M (1994) Organometallics 11:4129.CrossRefGoogle Scholar
  50. 9. (b)
    Watanuki S, Ochifuji N, Mori M (1995) Organometallics 14:5062CrossRefGoogle Scholar
  51. 10.
    Trost BM, Tanoury GJ (1988) J Am Chem Soc 110:1636CrossRefGoogle Scholar
  52. 11. (a)
    Trost BM, Trost MK (1991) J Am Chem Soc 113:1850.CrossRefGoogle Scholar
  53. 11. (b)
    Trost BM, Trost MK (1991) Tetrahedron Lett 32:3647.CrossRefGoogle Scholar
  54. 11. (c)
    Trost BM, Ynai M, Hoogsteen K (1993) J Am Chem Soc 115:5294.CrossRefGoogle Scholar
  55. 11. (d)
    Trost BM, Hashmi ASK (1994) J Am Chem Soc 116:2183.CrossRefGoogle Scholar
  56. 11. (e)
    Trost BM, Hashmi ASK (1993) Angew Chem Ed Engl 32:1085CrossRefGoogle Scholar
  57. 12.
    Trost BM, Chang VK (1993) Synthesis 824Google Scholar
  58. 13.
    Chatani N, Furukawa N, Sakurai H, Murai S ( 1996) Organometallics 15:901CrossRefGoogle Scholar
  59. 14.
    Chatani N, Morimoto T, Muto T, Murai S (1994) J Am Chem Soc 116:6049CrossRefGoogle Scholar
  60. 15.
    Chatani N, Furukawa N, Seki Y, Kataoka K, Murai S (1997) Abstracts of 44th Symposium on Organometallic Chemistry, Osaka, p 370Google Scholar
  61. 16. (a)
    Grubbs RH, Miller SJ, Fu GC ( 1995) Acc Chem Res 28:446.CrossRefGoogle Scholar
  62. 16. (b)
    Schwab P, France MB, Ziller JW, Grubbs RH (1995) Angew Chem Int Ed Engl 34:2039.CrossRefGoogle Scholar
  63. 16. (c)
    Schwab P, Grubbs RH, Ziller JW (1996) J Am Chem Soc 118:100CrossRefGoogle Scholar
  64. 17. (a)
    Kim SH, Bowden NB, Grubbs RH (1994) J Am Chem Soc 116:10801.CrossRefGoogle Scholar
  65. 17. (b)
    Kim SH, Zuercher WJ, Bowden NB, Grubbs RH (1996) J Org Chem 61:1073CrossRefGoogle Scholar
  66. 18.
    Kinoshita A, Mori M ( 1994) Synlett 1020Google Scholar
  67. 19.
    Hopf H, Kreutzer M (1991) Angew Chem Int Ed Eng 30:1127CrossRefGoogle Scholar
  68. 20. (a)
    Kinoshita A, Sakakibara N, Mori M (1997) Abstracts of 44th Symposium on Organometallic Chemistry p. 326, Osaka.Google Scholar
  69. 20. (b)
    Kinoshita A, Sakakibara N, Mori M (1997) J Am Chem Soc 119:12388CrossRefGoogle Scholar
  70. 21.
    Takahashshi T, Xi Z, Fischer R, Huo S, Xi C, Nakajima K (1997) J Am Chem Soc 119:4561CrossRefGoogle Scholar
  71. 22. (a)
    Kinoshita A, Mori M (1996) J Org Chem 61:8356.CrossRefGoogle Scholar
  72. 22. (b)
    Kinoshita A, Mori M (1997) Heterocycles (in press)Google Scholar
  73. 23.
    Barrett AGM, Baugh SPD, Braddock DC, Flack K, Gibson VC, Procopiou PA (1997) J Am Chem Soc 119:1375CrossRefGoogle Scholar
  74. 24.
    Hammer K, Undheim K (1977) Tetrahedron 53:10603CrossRefGoogle Scholar

Copyright information

© Springer-Verlag Berlin Heidelberg 1998

Authors and Affiliations

  • Miwako Mori

There are no affiliations available

Personalised recommendations