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Alkylation of Nucleophilic Carbon. Enolates and Enamines

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Advanced Organic Chemistry

Part of the book series: Advanced Organic Chemistry ((AOCB))

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Abstract

Carbon-carbon bond formation is the fundamental basis for the construction of the molecular framework in the synthesis of organic molecules. Many carbon-carbon bond-forming processes involve reaction between a nucleophilic carbon and an electrophilic one. The emphasis in this chapter is on enolate ions and enamines, two of the most useful kinds of carbon nucleophiles, and on their reactions with alkylating agents.

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General References

  1. D. E. Bergbreiter and M. Newcomb, in Asymmetric Synthesis, J. D. Morrison (ed.), Academic Press, New York, 1983, Chapter 9.

    Google Scholar 

  2. D. Caine, in Carbon-Carbon Bond Formation, Vol. 1, R. L. Augustine (ed.), Marcel Dekker, New York, 1979, Chapter 2.

    Google Scholar 

  3. A. G. Cook (ed.), Enamines: Synthesis, Structure and Reactions, Second Edition, Marcel Dekker, New York, 1988.

    Google Scholar 

  4. D. J. Cram, Fundamentals of Carbanion Chemistry, Academic Press, New York, 1965.

    Google Scholar 

  5. H. O. House, Modern Synthetic Reactions, Second Edition, W. A. Benjamin, Menlo Park, California, 1972, Chapter 9.

    Google Scholar 

  6. J. R. Jones, The Iionization of Carbon Acids, Academic Press, New York, 1973.

    Google Scholar 

  7. J. C. Stowell, Carbanions in Organic Synthesis, Wiley-Interscience, New York, 1979.

    Google Scholar 

  8. W. S. Matthews, J. E. Bares, J. E. Bartmess, F. G. Bordwell, F. J. Cornforth, G. E. Drucker, Z. Margolin, R. J. McCallum, G. J. McCollum, and N. E. Vanier, J. Am. Chem. Soc. 97, 7006 (1975).

    Article  CAS  Google Scholar 

  9. H. D. Zook, W. L. Kelly, and I. Y. Posey, J. Org. Chem. 33, 3477 (1968).

    Article  CAS  Google Scholar 

  10. H. O. House and M. J. Urnen, J. Org. Chem. 38, 1000 (1973).

    Article  CAS  Google Scholar 

  11. W. C. Still and M.-Y. Tsai, J. Am. Chem. Soc. 102, 3654 (1980).

    Article  CAS  Google Scholar 

  12. H. O. House and B. M. Trost, J. Org. Chem. 30, 1341 (1965).

    Article  CAS  Google Scholar 

  13. D. Caine and T. L. Smith, Jr., J. Am. Chem. Soc. 102, 7568 (1980).

    Article  CAS  Google Scholar 

  14. M. F. Semmelhack, S. Tomoda, and K. M. Hurst, J. Am. Chem. Soc. 102, 7567 (1980).

    Article  CAS  Google Scholar 

  15. R. A. Lee, C. McAndrews, K. M. Patel, and W. Reusch, Tetrahedron Lett, 965 (1973).

    Google Scholar 

  16. R. H. Frazier, Jr., and R. L. Harlow, J. Org. Chem. 45, 5408 (1980).

    Article  CAS  Google Scholar 

  17. M. Gall and H. O. House, Org. Synth. 52, 39 (1972).

    CAS  Google Scholar 

  18. P. S. Wharton and C. E. Sundin, J. Org. Chem. 33, 4255 (1968).

    Article  CAS  Google Scholar 

  19. B. W. Rockett and C. R. Hauser, J. Org. Chem. 29, 1394 (1964).

    Article  CAS  Google Scholar 

  20. J. Meier, Bull. Soc. Chim. Fr., 290 (1962).

    Google Scholar 

  21. M. E. Jung and C. A. McCombs, Org. Synth. 58, 163 (1978).

    CAS  Google Scholar 

  22. H. O. House, T. S. B. Sayer, and C.-C. Yau, J. Org. Chem. 43, 2153 (1978).

    Article  CAS  Google Scholar 

  23. J. M. Harless and S. A. Monti, J. Am. Chem. Soc. 96, 4714 (1974).

    Article  CAS  Google Scholar 

  24. A. Wissner and J. Meinwald, J. Org. Chem. 38, 1967 (1973).

    Article  Google Scholar 

  25. W. J. Gensler and P. H. Solomon, J. Org. Chem. 38, 1726 (1973).

    Article  CAS  Google Scholar 

  26. H. W. Whitlock, Jr., J. Am. Chem. Soc. 84, 3412 (1962).

    Article  CAS  Google Scholar 

  27. C. H. Heathcock, R. A. Badger, and J. W. Patterson, Jr., J. Am. Chem. Soc. 89, 4133 (1967).

    Article  CAS  Google Scholar 

  28. E. J. Corey and D. S. Watt, J. Am. Chem. Soc. 95, 2302 (1973).

    Google Scholar 

  29. W. G. Kofron and L. G. Wideman, J. Org. Chem. 37, 555 (1972).

    Article  CAS  Google Scholar 

  30. C. R. Hauser, T. M. Harris, and T. G. Ledford, J. Am. Chem. Soc. 81, 4099 (1959).

    Article  CAS  Google Scholar 

  31. N. Campbell and E. Ciganek, J. Chem. Soc, 3834 (1956).

    Google Scholar 

  32. F. W. Sum and L. Weiler, J. Am. Chem. Soc. 101, 4401 (1979).

    Article  CAS  Google Scholar 

  33. K. W. Rosemund, H. Herzberg, and H. Schutt, Chem. Ber. 87, 1258 (1954).

    Article  Google Scholar 

  34. T. Hudlicky, F. J. Koszyk, T. M. Kutchan, and J. P. Sheth, J. Org. Chem. 45, 5020 (1980).

    Article  CAS  Google Scholar 

  35. C. R. Hauser and W. R. Dunnavant, Org. Synth. 40, 38 (1960).

    CAS  Google Scholar 

  36. G. Opitz, H. Milderberger, and H. Suhr, Justus Liebigs Ann. Chem., 649, 47 (1961).

    Article  CAS  Google Scholar 

  37. K. Wiesner, K. K. Chan, and C. Demerson, Tetrahedron Lett., 2893 (1965).

    Google Scholar 

  38. K. Shimo, S. Wakamatsu, and T. Inoüe, J. Org. Chem. 26, 4868 (1961).

    Article  CAS  Google Scholar 

  39. T. A. Spencer, K. K. Schmiegel, and K. L. Williamson, J. Am. Chem. Soc. 85, 3785 (1963).

    Article  CAS  Google Scholar 

  40. G. R. Kieczkowski and R. H. Schlessinger, J. Am. Chem. Soc 100, 1938 (1978).

    Article  Google Scholar 

  41. d. E. D. Bergmann, D. Ginsburg, and R. Pappo, Org. React. 10, 179 (1959).

    CAS  Google Scholar 

  42. L. Mandell, J. U. Piper, and K. P. Singh, J. Org. Chem. 28, 3440 (1963).

    Article  CAS  Google Scholar 

  43. H. O. House, W. A. Kleschick, and E. J. Zaiko, J. Org. Chem. 43, 3653 (1978).

    Article  CAS  Google Scholar 

  44. J. E. McMurry and J. Melton, Org. Synth. 56, 36 (1977).

    CAS  Google Scholar 

  45. D. F. Taber and B. P. Gunn, J. Am. Chem. Soc. 101, 3992 (1979).

    Article  CAS  Google Scholar 

  46. H. Feuer, A. Hirschfeld, and E. D. Bergmann, Tetrahedron 24, 1187 (1968).

    Article  CAS  Google Scholar 

  47. A. Baradel, R. Longeray, J. Dreux, and J. Doris, Bull. Soc. Chim. Fr., 255 (1970).

    Google Scholar 

  48. H. H. Baer and K. S. Ong, Can. J. Chem. 46, 2511 (1968).

    Article  CAS  Google Scholar 

  49. A. Wettstein, K. Heusler, H. Ueberwasser, and P. Wieland, Helv. Chim. Ada 40, 323 (1957).

    Article  CAS  Google Scholar 

  50. E. Wenkert and D. P. Strike, J. Org. Chem. 27, 1883 (1962).

    Article  CAS  Google Scholar 

  51. S. J. Etheredge, J. Org. Chem. 31, 1990 (1966).

    Article  CAS  Google Scholar 

  52. R. Deghenghi and R. Gaudry, Tetrahedron Lett., 489 (1962).

    Google Scholar 

  53. P. A. Grieco and C. C. Pogonowski, J. Am. Chem. Soc. 95, 3071 (1973).

    Article  CAS  Google Scholar 

  54. E. M. Kaiser, W. G. Kenyon, and C. R. Hauser, Org. Synth. V, 559 (1973).

    Google Scholar 

  55. J. Cason, Org. Synth. IV, 630 (1963).

    Google Scholar 

  56. S. A. Glickman and A. C. Cope, J. Am. Chem. Soc. 67, 1012 (1945).

    Article  CAS  Google Scholar 

  57. W. Steglich and L. Zechlin, Chem. Ber. III, 3939 (1978).

    Article  Google Scholar 

  58. S. F. Brady, M. A. Ilton, and W. S. Johnson, J. Am. Chem. Soc. 90, 2882 (1968).

    Article  CAS  Google Scholar 

  59. R. P. Hatch, J. Shringarpure, and S. M. Weinreb, J. Org. Chem. 43, 4172 (1978).

    Article  CAS  Google Scholar 

  60. S. Masamune, J. Am. Chem. Soc. 86, 288 (1964).

    Article  CAS  Google Scholar 

  61. E. J. Corey, M. Ohno, R. B. Mitra, and P. A. Vatakencherry, J. Am. Chem. Soc. 86, 478 (1964).

    Article  CAS  Google Scholar 

  62. J. Fried, in Heterocyclic Compounds, R. C. Elderfield (ed.), Vol. 1, Wiley, New York, 1950, p. 358.

    Google Scholar 

  63. R. Chapurlat, J. Huet, and J. Druex, Bull. Soc. Chim. Fr., 2446, 2450 (1967).

    Google Scholar 

  64. F. Kuo and P. L. Fuchs, J. Am. Chem. Soc. 109, 1122 (1987).

    Article  CAS  Google Scholar 

  65. L. A. Paquette, H.-S. Lin, D. T. Belmont, and J. P. Springer, J. Org. Chem. 51, 4807 (1986).

    Article  CAS  Google Scholar 

  66. R. K. Boeckman, Jr., D. K. Heckenden, and R. L. Chinn, Tetrahedron Lett. 28, 3551 (1987).

    Article  CAS  Google Scholar 

  67. D. Seebach, J. D. Aebi, M. Gander-Coquot, and R. Naef, Helv. Chim. Acta 70, 1194 (1987).

    Article  CAS  Google Scholar 

  68. F. E. Ziegler, S. I. Klein, U. K. Pati, and T.-F. Wang, J. Am. Chem. Soc. 107, 2730 (1985).

    Article  CAS  Google Scholar 

  69. M. E. Kuehne, J. Org. Chem. 35, 171 (1970).

    Article  CAS  Google Scholar 

  70. D. A. Evans, S. L. Bender, and J. Morris, J. Am. Chem. Soc. 110, 2506 (1988).

    Article  CAS  Google Scholar 

  71. K. Tomioka, Y.-S. Cho, F. Sato, and K. Koga, J. Org. Chem. 53, 4094 (1988).

    Article  CAS  Google Scholar 

  72. K. Tomioka, H. Kawasaki, K. Yasuda, and K. Koga, J. Am. Chem. Soc. 110, 3597 (1988).

    Article  CAS  Google Scholar 

  73. T. Kametani, Y. Suzuki, H. Furuyama, and T. Honda, J. Org. Chem. 48, 31 (1983).

    Article  CAS  Google Scholar 

  74. R. A. Kjonaas and D. D. Patel, Tetrahedron Lett. 25, 5467 (1983).

    Article  Google Scholar 

  75. D. F. Taber and R. E. Ruckle, Jr., J. Am. Chem. Soc. 108, 7686 (1986).

    Article  CAS  Google Scholar 

  76. M. Yamaguchi, M. Tsukamoto, and I. Hirao, Tetrahedron Lett. 26, 1723 (1985).

    Article  CAS  Google Scholar 

  77. D. L. Snitman, M.-Y. Tsai, D. S. Watt, C. L. Edwards, and P. L. Stotter, J. Org. Chem. 44, 2838 (1979).

    Article  CAS  Google Scholar 

  78. A. G. Schultz and J. P. Dittami, J. Org. Chem. 48, 2318 (1983).

    Article  CAS  Google Scholar 

  79. J. G. Henkel and L. A. Spurlock, J. Am. Chem. Soc. 95, 8339 (1973).

    Article  CAS  Google Scholar 

  80. M. S. Newman, V. DeVries, and R. Darlak, J. Org. Chem. 31, 2171 (1966).

    Article  CAS  Google Scholar 

  81. P. A. Manis and M. W. Rathke, J. Org. Chem. 45, 4952 (1980).

    Article  CAS  Google Scholar 

  82. F. D. Lewis, T.-I. Ho, and R. J. DeVoe, J. Org. Chem. 45, 5283 (1980).

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. University of Virginia, Charlottesville, Virginia, USA

    Francis A. Carey & Richard J. Sundberg

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  1. Francis A. Carey
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  2. Richard J. Sundberg
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© 1990 Plenum Press, New York

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Carey, F.A., Sundberg, R.J. (1990). Alkylation of Nucleophilic Carbon. Enolates and Enamines. In: Advanced Organic Chemistry. Advanced Organic Chemistry. Springer, Boston, MA. https://doi.org/10.1007/978-1-4613-9797-7_1

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  • DOI: https://doi.org/10.1007/978-1-4613-9797-7_1

  • Publisher Name: Springer, Boston, MA

  • Print ISBN: 978-0-306-43457-0

  • Online ISBN: 978-1-4613-9797-7

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