Intramolecular [2+2] Cycloadditons of Ketenes and Olefins

  • Beat Ernst
  • Alain de Mesmaeker
  • Hans Greuter
  • Siem J. Veenstra
Part of the NATO ASI Series book series (ASIC, volume 273)

Abstract

The synthetic potential of the intramolecular ketene cycloaddition is presented. It proves to be a versatile method for the synthesis of a variety of bi- and tricyclic cyclobutanones. The major side reaction, namely the dimerization of the ketene is prevented by the introduction of conformational restrictions. This has been achieved by an additional double bond or by an annulated ring system. Following this strategy C-analogues of a penem and a carbapenem as well as linear and angular annulated triquinanes are obtained in high yield.

Keywords

Acid Chloride Unsaturated Ester Double Bond Migration Aldol Product Additional Double Bond 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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REFERENCES

  1. [1]
    H. Staudinger, Chem. Ber. 44 (1911) 521.CrossRefGoogle Scholar
  2. [2]
    H.K. Hal1, D.E. Plorde, US-Pat. 3646150 (1968), Du Pont.Google Scholar
  3. [3]
    W.T. Brady, O.H. Waters, J. Org. Chem. 32 (1967) 3703.CrossRefGoogle Scholar
  4. [4]
    J.B. Sieja, J. Am. Chem. Soc. 93 (1971) 130.CrossRefGoogle Scholar
  5. [5]
    R.R. Sauers, K.W. Kelly, J. Org. Chem. 35 (1970) 3286.CrossRefGoogle Scholar
  6. [6a]
    J.J. Beereboom, J. Am. Chem. Soc. 85 (1963) 3525; J. Org. Chem. 30 (1963) 4230Google Scholar
  7. [6b]
    W.F. Erman, J. Am. Chem. Soc. 91 (1969) 779CrossRefGoogle Scholar
  8. [6c]
    S.W. Baldwin, E.H. Page, J. Chem. Soc. Chem. Commun. 1972, 1337Google Scholar
  9. [6d]
    F. Leyendecker, R. Bloch, J.M. Conia, Tetrahedron Lett. 1972, 3703Google Scholar
  10. [6e]
    R.H. Bisceglia, C.J. Cheer, J. Chem. Soc. Chem. Commun. 1973, 165Google Scholar
  11. [6f]
    S. Moon, T.F. Kolesar, J. Org. Chem. 39 (1974) 995CrossRefGoogle Scholar
  12. [6g]
    L. Libit, US-Pat. 4005109 (1974)Google Scholar
  13. [6h]
    A. Smit, J.G.J. Kok, H.W. Geluk, J. Chem. Soc. Chem. Commun. 1975, 513Google Scholar
  14. [6i]
    F. Leyendecker, Tetrahedron 32 (1976) 349CrossRefGoogle Scholar
  15. [6j]
    T. Sasaki, S. Eguchi, Y. Hirako, J. Org. Chem. 42 (1977) 2981CrossRefGoogle Scholar
  16. [6k]
    A. Maujean, G. Marcy, J. Cuche, J. Chem. Soc. Chem. Commun. 1980, 92Google Scholar
  17. [6l]
    M. Kuzuya, F. Miyake, T. Okuda, Tetrahedron Lett. 1980, 1043 and 2185Google Scholar
  18. [6m]
    A. Alder, D. Bellus, J. Am. Chem. Soc. 105 (1983) 6712CrossRefGoogle Scholar
  19. [6n]
    H. Dhimane, J.C. Pommelet, J. Cuche, Tetrahedron Lett. 26 (1985) 833CrossRefGoogle Scholar
  20. [6o]
    F. Arya, J. Bouquant, J. Cuche, Tetrahedron Lett. 27 (1986) 1913.CrossRefGoogle Scholar
  21. [7a]
    W.F. Erman, J. Am. Chem. Soc. 89 (1967) 3828CrossRefGoogle Scholar
  22. [7b]
    O.L. Chapman, J.D. Lassila, J. Am. Chem. Soc. 90, (1968) 2449CrossRefGoogle Scholar
  23. [7c]
    O.L. Chapman, M. Kane, J.D. Lassila, R.L. Loeschen, H.E. Wright, J. Am. Chem. Soc. 91 (1969) 6856CrossRefGoogle Scholar
  24. [7d]
    A.S. Kende, Z. Goldschmit, P.T. Izzo, J. Am. Chem. Soc. 91 (1969) 6858CrossRefGoogle Scholar
  25. [7e]
    H. Hart, G.M. Lowe, J. Am. Chem. Soc. 93 (1971) 6266CrossRefGoogle Scholar
  26. [7f]
    D. Becker, M. Nagler, D. Birnbaum, J. Am. Chem. Soc. 94 (1972) 4771CrossRefGoogle Scholar
  27. [7g]
    Z. Goldschmit, U. Gutman, Y. Bakal, A. Worchel, Tetrahedron Lett. 1973, 3759Google Scholar
  28. [7h]
    D. Becker Z. Harel, D. Birnbaum, J. Chem. Soc. Chem. Commun. 1975, 377Google Scholar
  29. [7i]
    S. Ayral-Kaloustian, S. Wolff, W.C. Agosta, J. Org. Chem. 43 (1978) 3314CrossRefGoogle Scholar
  30. [7j]
    D. Becker, D. Birnbaum, J. Org. Chem. 45 (1980) 570CrossRefGoogle Scholar
  31. [7k]
    R.E. Ireland, J.D. Godfrey, S. Thaisrivongs, J. Am. Chem Soc. 103 (1981) 2446CrossRefGoogle Scholar
  32. [7l]
    E. Lee-Ruff, A.C. Hopkinson, H. Kazarians-Moghaddam, Tetrahedron Lett. 24 (1983) 2067CrossRefGoogle Scholar
  33. [7m]
    A.G. Schultz, J.P. Dittami, K.K. Eng, Tetrahedron Lett. 25 (1984) 255.CrossRefGoogle Scholar
  34. [8]
    L. Ghosez, M.J. O’Donnell in Pericyclic Reactions, A.P. Marchand R.E. Lehr, Eds., Academic Press, New York, 1977, Vol. 2, p. 79–140.Google Scholar
  35. [9a]
    M. Kuzuya, F. Miyake, T. Okuda, J. Chem. Soc. Perkin Trans. II, 1984, 1471Google Scholar
  36. [9b]
    E. Sonveaux, J.M. Andre, J. Delhalle, J.G. Fripiat, Bull. Soc. Chim. Belg. 94, (1985) 831.CrossRefGoogle Scholar
  37. [10]
    G.B. Payne, J. Org. Chem. 31 (1966) 718.CrossRefGoogle Scholar
  38. [11]
    I. Markó, B. Ronsmans, A.-M. Hesbain-Frisque, S. Dumas, L. Ghosez, B. Ernst, H. Greuter, J. Am. Chem. Soc. 107 (1985) 2192.CrossRefGoogle Scholar
  39. [12]
    I. Fleming in Frontier Orbitals and Organic Chemical Reactions, J. Wiley & Sons, 1976, 143 ff.Google Scholar
  40. [13a]
    Y.S. Kulkarni, B.B. Snider, J. Org. Chem. 50 (1985) 2809CrossRefGoogle Scholar
  41. [13b]
    Y.S. Kulkarni, B.W. Burbaum, B.B. Snider, Tetrahedron Lett. 26 (1985) 5619CrossRefGoogle Scholar
  42. [13c]
    B.B. Snider, E. Ron, B.W. Burbaum, J. Org. Chem. 52 (1987) 5413.CrossRefGoogle Scholar
  43. [14]
    E.J. Corey, M.C. Desai, Tetrahedron Lett. 26 (1985) 3535.CrossRefGoogle Scholar
  44. [15]
    M.I. Page, Acc. Chem. Res. 17 (1984) 144.CrossRefGoogle Scholar
  45. [16a]
    E.M. Gordon, J. Pluščec, M.A. Ondetti, Tetrahedron Lett. 22 (1981) 1871CrossRefGoogle Scholar
  46. [16b]
    G.A. Boswell, Jr., A.J. Cocuzza, US-Pat. 4 505 905 (1982), Du PontGoogle Scholar
  47. [16c]
    O. Meth-Cohn, A.J. Reason, S.M. Roberts, J. Chem. Soc. Chem. Commun. 1982, 90Google Scholar
  48. [16d]
    G. Lowe, S. Swain, ibid. 1983, 1279Google Scholar
  49. [16e]
    A.J. Cocuzza, G.A. Boswell, Tetrahedron Lett. 26 (1985) 5363CrossRefGoogle Scholar
  50. [16f]
    G. Lowe, S. Swain, J. Chem. Soc., Perkin Trans, I 1985, 391CrossRefGoogle Scholar
  51. [16g]
    G. Lange, M.E. Savard, T. Viswanatha, G.I. Dmitrienko, Tetrahedron Lett. 26 (1985) 1791CrossRefGoogle Scholar
  52. [16h]
    D. Agathocleous, G. Cox, M.I. Page, Tetrahedron Lett. 27 (1986) 1631.CrossRefGoogle Scholar
  53. [17]
    H. Muruyama, T. Hiraoka, J. Org. Chem. 51 (1986) 399 and references cited herein.CrossRefGoogle Scholar
  54. [18]
    Prepared by Dr. P. Schneider, Pharmaceuticals Division, CIBA-GEIGY Ltd., CH-4002 Basel.Google Scholar
  55. [19]
    A. Wissner, C.V. Grudzinskas, J. Org. Chem. 43 (1978) 3972.CrossRefGoogle Scholar
  56. [20]
    The analogous reaction with vinyl lithium was described: C.L. Semmelhack, I.-C. Chiu, K.G. Grohman, J. Am. Chem. Soc. 98 (1976) 2005.CrossRefGoogle Scholar
  57. [21]
    B. Haveaux, A. Dekoker, M. Rens, A.R. Sidani, J. Toye, L. Ghosez, Org. Synth. 59, 26.Google Scholar
  58. [22]
    L. Lombardo, Tetrahedron Lett. 26 (1985) 381.CrossRefGoogle Scholar
  59. [23a]
    J.E. Baldwin, M.C. McDaniel, J. Am. Chem. Soc. 89 (1967) 1537CrossRefGoogle Scholar
  60. [23b]
    J.E. Baldwin, M.C. McDaniel, J. Am. Chem. Soc. 90 (1968) 6118.CrossRefGoogle Scholar
  61. [24]
    H. Mayr, R. Huisgen, Ang. Chem. 87 (1975) 491.Google Scholar
  62. [25]
    C. Exon, P. Magnus, J. Am. Chem. Soc. 105 (1983) 2477 and references cited therein.CrossRefGoogle Scholar
  63. [26]
    R.L. Funk, G.L. Bolton, J. Org. Chem. 49 (1984) 5021 and references cited therein.CrossRefGoogle Scholar
  64. [27a]
    L.A. Paquette, Y.-K. Han, J. Am. Chem. Soc. 103 (1981) 1835CrossRefGoogle Scholar
  65. [27b]
    P.A. Wender, G.B. Dreyer, Tetrahedron 37 (1981) 4445CrossRefGoogle Scholar
  66. [27c]
    M.C. Pirrung, J. Am. Chem. Soc. 103 (1981) 82 and references cited therein.CrossRefGoogle Scholar
  67. [28]
    G.D. Annis, L.A. Paquette, J. Am. Chem. Soc. 104 (1982) 4504.CrossRefGoogle Scholar
  68. [29]
    H. Schostarez, L.A. Paquette, J. Am. Chem. Soc. 103 (1981) 722.CrossRefGoogle Scholar
  69. [30]
    A. De Mesmaeker, S.J. Veenstra, B. Ernst, Tetrahedron Lett. 29 (1988) 459.CrossRefGoogle Scholar
  70. [31]
    The allylcyclopentanone 77 was prepared in three steps from cyclopentanone via allylation of the corresponding dimethylhydrazone (overall yield 72 %) in analogy with E.J. Corey, D. Enders, Tetrahedron Lett. 1976, 3.Google Scholar
  71. [32]
    For deconjugation of α,b-unsaturated esters during Horner- Emmons and Peterson olefination seeGoogle Scholar
  72. [32a]
    S.L. Hartzell, D.F. Sullivan, M.W. Rathke, Tetrahedron Lett. 1974, 1403Google Scholar
  73. [32b]
    H. Taguchi, Soc. Jpn. 47 (1974) 2529.Google Scholar
  74. [33]
    J.R. Stille, R.H. Grubbs, J. Am. Chem. Soc. 108 (1986) 855.CrossRefGoogle Scholar
  75. [34]
    S.J. Veenstro, A. De Mesmaeker, B. Ernst, Tetrahedron Lett. 29 (1988) 2303.CrossRefGoogle Scholar
  76. [35]
    P. Beak, D.J. Kempf, K.D. Wilson, J. Am. Chem. Soc. 107 (1985) 4745.CrossRefGoogle Scholar
  77. [36]
    J.S. Yadav, B.V. Joshi, V.R. Gadgil, Indian J. Chem., Sect. B 26 (1987) 399.Google Scholar
  78. [37]
    The autors thank Dr. D. Poppinger, Zentrale Funktion Forschung, Computer Chemistry, Ciba-Geigy Ltd., CH-4002 Basel for the calculations according to: M.J.S. Dewar, E.G. Zoebisch, E.F. Healy, J.J.P. Stewart, J. Am. Chem. Soc. 107 (1985) 3902; Quantum Chemistry Program Exchange Nr. 506.CrossRefGoogle Scholar
  79. [38]
    H. Marschal1, F. Vogel, Chem. Ber. 107 (1974) 2176.CrossRefGoogle Scholar
  80. [39]
    Y. Fukuda, T. Negoro, Y. Tobe, K. Kimura, Y. Odaira, J. Org. Chem. 44 (1979) 4557.CrossRefGoogle Scholar
  81. [40]
    L. Ghosez, I. Markó, A.-M. Hesbain-Frisque, Tetrahedron Lett. 27 (1986) 5211.CrossRefGoogle Scholar
  82. [41a]
    B.B. Snider, R.A.H.F. Hui, Y.S. Kulkarni, J. Am. Chem. Soc. 107 (1985) 2194CrossRefGoogle Scholar
  83. [41b]
    B.B. Snider, R.A.H.F. Hui, J. Org. Chem. 50 (1985) 5167.CrossRefGoogle Scholar
  84. [42a]
    W.T. Brady, Y.F. Giang, J. Org. Chem. 50 (1985) 5177CrossRefGoogle Scholar
  85. [42b]
    W.T. Brady, Y.F. Giang, A.P. Marchand, A.H. Wu, J. Org. Chem. 52 (1987) 3457CrossRefGoogle Scholar
  86. [42c]
    W.T. Brady, A.P. Marchand, Y.F. Giang, A.H. Wu, Synthesis 1987 395.Google Scholar
  87. [43]
    E.J. Corey, M.C. Desai, T.A. Engler, J. Am. Chem. Soc. 107 (1985) 4339.CrossRefGoogle Scholar
  88. [44]
    W. Oppolzer, A. Nakao, Tetrahedron Lett. 27 (1986) 5471.CrossRefGoogle Scholar
  89. [45]
    H.-U. Reisig, Nachr. Chem. Tech. Lab. 34 (1986) 880.Google Scholar

Copyright information

© Kluwer Academic Publishers 1989

Authors and Affiliations

  • Beat Ernst
    • 1
  • Alain de Mesmaeker
    • 1
  • Hans Greuter
    • 1
  • Siem J. Veenstra
    • 1
  1. 1.Central Research LaboratoriesCIBA-GEIGY Ltd.BaselSwitzerland

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