Skip to main content

Asymmetric Homogeneous Catalysis by Chiral Transition Metal Complexes

  • Chapter
Fundamental Research in Homogeneous Catalysis

Abstract

Asymmetric catalysis is the most common way to synthesize single antipodes in biological processes.4 It would also be the most convenient way to prepare optically active compounds in the laboratory since in principle very small amounts of antipodes could be used to synthesize an unlimited quantity of a chiral compound having a specific chirality. In spite of this, asymmetric catalysis, with the exception of enzymatic catalysis, was very little investigated until the early sixties.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

eBook
USD 16.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. J. B. Jones, J. F. Beck, “Application of Biochemical Systems in Organic Synthesis” Part I, J. B. Jones, C. J. Sih, D. Perlman, Ed., Wiley, New York, N.Y., 1976, p. 107–401.

    Google Scholar 

  2. G. Bredig, P. S. Fiske, Biochem. Z., 46, 7 (1912).

    Google Scholar 

  3. V. Prelog, M. Wilhelm, Helv. Chim. Acta, 37, 1634 (1954).

    Article  CAS  Google Scholar 

  4. For a review see: H. Pracejus, Fortsch. Chem. Forsch., 8, 493 (1967).

    Article  CAS  Google Scholar 

  5. H. Pracejus, Ann., 634, 9 (1960).

    CAS  Google Scholar 

  6. G. Berti, A. Marsili, Angew. Chem., 75, 1026 (1963).

    Article  Google Scholar 

  7. G. Natta, P. Pino, P. Corradini, F. Danusso, E. Mantica, G. Mazzanti, G. Moraglio, J. Amer. Chem. Soc., 77, 1708 (1955).

    Article  CAS  Google Scholar 

  8. C.E. Schildknecht, S. F. Gross, H. R. Davidson, J. M. Lambert, A. Zoss, Ind. Eng. Chem., 40, 2108 (1948).

    Article  Google Scholar 

  9. A. A. Morton, Ind. Eng. Chem., 42, 1488 (1950).

    CAS  Google Scholar 

  10. J. D. Morrison, H. S. Mosher, “Asymmetric Organic Reactions,” Prentice-Hall, Inc., Englewood Cliffs, N.J., 1971, p. 425.

    Google Scholar 

  11. For a review see: P. Pino, U. W. Suter, Polymer, 17, 977 (1976).

    Article  CAS  Google Scholar 

  12. S. Akabori, Y. Izumi, Y. Fuji, S. Sakurai, Nature, 178, 323 (1956).

    Article  CAS  Google Scholar 

  13. For a review see: Y. Izumi, Angew. Chem., 83, 956 (1971).

    Article  Google Scholar 

  14. E. L. Eliel, “Stereochemistry of Carbon Compounds,” International Student Edition, McGraw Hill, New York, 1962, p. 76.

    Google Scholar 

  15. M. Raban, K. Mislow, Topics in Stereochemistry, N. L. Allinger and E. L. Eliel Eds., Vol. 2, 1967, p. 199.

    Chapter  Google Scholar 

  16. See ref. 10, p. 10ff.

    Google Scholar 

  17. Y. Orito, S. Niwa, S. Imai, Yuki Gosei Kagaku Kyokai Shi, 34, 672 (1976);

    Article  CAS  Google Scholar 

  18. Y. Orito, S. Niwa, S. Imai, C. A., 86, 43148 (1977).

    Google Scholar 

  19. G. Natta, L. Porri, S. Valenti, Makromol. Chem., 67, 225 (1963).

    Article  CAS  Google Scholar 

  20. J. Furukawa, T. Kakuzen, H. Morikawa, R. Yamamoto, O. Okuno, Bull. Chem. Soc. Japan, 41, 155 (1968).

    Article  CAS  Google Scholar 

  21. K. R. Hanson, J. Amer. Chem. Soc, 88, 2731 (1966).

    Article  CAS  Google Scholar 

  22. See ref. 14, p. 68.

    Google Scholar 

  23. R. S. Cahn, C. Ingold, V. Prelog, Angew. Chem., 78, 413 (1966).

    Article  Google Scholar 

  24. This nomenclature has been proposed for the first time by some authors in a Japanese book: “Chemistry of Asymmetric Reactions” Kagaku Sosetsu No. 4, 1974 (see, for example, C. A., 82, 30459 (1975)).

    Google Scholar 

  25. G. Consiglio, C. Botteghi, Helv. Chim. Acta, 56, 460 (1973).

    Article  CAS  Google Scholar 

  26. Y. Kiso, K. Tamao, N. Miyake, K. Yamamoto, M. Kumada, Tetrahedron Lett., 3 (1974).

    Google Scholar 

  27. T. Hayashi, M. Tajika, K. Tamao, M. Kumada, J. Amer. Chem. Soc, 98, 3718 (1976).

    Article  CAS  Google Scholar 

  28. F. R. Jensen, K. L. Nakamaye, J. Amer. Chem. Soc, 88, 3437 (1966) and references therein.

    Article  CAS  Google Scholar 

  29. W. S. Knowles, M. J. Sabacky, Chem. Comm., 1445 (1968).

    Google Scholar 

  30. C. Botteghi, G. Consiglio, P. Pino, Chimia, 26, 141 (1972).

    CAS  Google Scholar 

  31. K. Yamamoto, T. Hayashi, M. Kumada, J. Amer. Chem. Soc, 93, 5301 (1971).

    Article  CAS  Google Scholar 

  32. B. Bogdanović, B. Henc, H. G. Karman, H. G. Nuessel, D. Walter, G. Wilke, Ind. Eng. Chem., 62 (12), 35 (1970).

    Google Scholar 

  33. W. S. Knowles, M. J. Sabacky, B. D. Vineyard, D. J. Weinkauff, J. Amer. Chem. Soc, 97, 2567 (1975) and therein references.

    Article  CAS  Google Scholar 

  34. H. B. Kagan, Pure Appl. Chem., 43, 401 (1975) and therein references.

    Article  CAS  Google Scholar 

  35. L. Horner, H. Siegel, Phosphorus, 1, 209 (1972) and therein references.

    CAS  Google Scholar 

  36. P. Abley, F. J. McQuillin, J. Chem. Soc. (c), 844 (1971).

    Google Scholar 

  37. T. Hayashi, T. Mise, S. Mitachi, K. Yamamoto, M. Kumada, Tetrahedron Lett., 1133 (1976).

    Google Scholar 

  38. M. Tanaka, I. Ogata, J. C. S. Chem. Comm., 735 (1975).

    Google Scholar 

  39. M. Fiorini, G. M. Giongo, F. Marcati, Y. Marconi, J. Mol. Cat., 1, 451 (1976).

    Article  CAS  Google Scholar 

  40. S. Takeuchi, Y. Ohgo, J. Yoshimura, Chem. Lett., 265 (1973).

    Google Scholar 

  41. B. R. James, D. K. W. Wang, R. F. Voigt, J. C. S. Chem. Comm., 574 (1975).

    Google Scholar 

  42. B. R. James, R. S. McMillan, K. J. Reimer, J. Mol. Catal., 1, 439 (1976).

    Article  CAS  Google Scholar 

  43. For a review, see, J. D. Morrison, W. F. Masler, M. K. Neuberg, Adv. Catal., 26, 8l (1976).

    Google Scholar 

  44. T. Hayashi, M. Tanaka, I. Ogata, Tetrahedron Lett., 295 (1977).

    Google Scholar 

  45. K. Achiwa, J. Amer. Chem. Soc., 98, 8265 (1976).

    Article  CAS  Google Scholar 

  46. P. Bonvicini, A. Levi, G. Modena, G. Scorrano, J. C. S. Chem. Comm., 1188 (1972).

    Google Scholar 

  47. M. Tanaka, Y. Watanahe, T. Mitsudo, H. Ivane, Y. Takegami, Chem. Lett., 239 (1973).

    Google Scholar 

  48. J. Solodar, Chem. Techn., 421 (1975).

    Google Scholar 

  49. B. Heil, S. Toros, S. Vastag, L. Marko, J. Organometal. Chem., 94, C47 (1975).

    Article  CAS  Google Scholar 

  50. C. Botteghi, M. Bianchi, E. Benedetti, U. Matteoli, Chimia, 29, 256 (1975).

    CAS  Google Scholar 

  51. A. Levi, G. Modena, G. Scorrano, J. C. S. Chem. Comm., 6 (1975).

    Google Scholar 

  52. R. W. Waldron, J. H. Weher, Inorg. Chim. Acta, 18, L3 (1976).

    Article  CAS  Google Scholar 

  53. T. Hayashi, T. Mise, M. Kumada, Tetrahedron Lett., 4351 (1976).

    Google Scholar 

  54. Y. Ohgo, Y. Natori, S. Takeuchi, J. Yoshimura, Chem. Lett., 1327 (1974) and therein references.

    Google Scholar 

  55. H. B. Kagan, N. Langlois, T. P. Dang, J. Organometal. Chem., 90, 353 (1975).

    Article  CAS  Google Scholar 

  56. P. Pino, G. Consiglio, C. Botteghi, C. Salomon, Adv. Chem. Ser., 132, 295 (1974) and references therein.

    Article  CAS  Google Scholar 

  57. G. Consiglio, P. Pino, Chimia, 30, 193 (1976) and references therein.

    CAS  Google Scholar 

  58. G. Consiglio, P. Pino, Helv. Chim. Acta, 59, 642 (1976).

    Article  CAS  Google Scholar 

  59. M. Tanaka, Y. Watanabe, T. Mitsudo, Y. Takegami, Bull. Chem. Soc. Japan, 47, 1698 (1974) and references therein.

    Article  CAS  Google Scholar 

  60. R. Stern, A. Hirschauer, L. Sajus, Tetrahedron Lett., 3247 (1973).

    Google Scholar 

  61. A. Stefani, D. Tatone, Helv. Chim. Acta, 60, 5l8 (1977).

    Article  Google Scholar 

  62. K. Yamamoto, T. Hayashi, Y. Uramoto, R. Ito, M. Kumada, J. Organometal. Chem., 118, 331 (1976) and references therein.

    Article  CAS  Google Scholar 

  63. R. J. P. Corriu, J. J. E. Moreau, J. Organometal. Chem., 85, 19 (1975).

    Article  CAS  Google Scholar 

  64. T. Hayashi, K. Yamamoto, M. Kumada, J. Organometal. Chem., 112, 253 (1976) and references therein.

    Article  CAS  Google Scholar 

  65. T. Hayashi, K. Yamamoto, K. Kasuga, H. Omizu, M. Kumada, J. Organometal. Chem., 113, 127 (1976) and references therein.

    Article  CAS  Google Scholar 

  66. J. Benes, J. Hetflejs, Coll. Czec. Chem. Comm., 41, 2264 (1976).

    Article  CAS  Google Scholar 

  67. I. Ojima, T. Kogure, M. Kumagai, S. Horiuchi, T. Sato, J. Organometal. Chem., 122, 83 (1976) and references therein.

    Article  CAS  Google Scholar 

  68. N. Langlois, T. P. Dang, H. B. Kagan, Tetrahedron Lett., 4865 (1973).

    Google Scholar 

  69. B. Bogdanovic, B. Henc, A. Loesler, B. Meister, H. Pauling, G. Wilke, Angew. Chem., 85, 1013 (1973) and references therein.

    Article  CAS  Google Scholar 

  70. H. Nozaki, H. Takaya, S. Moriuti, R. Noyori, Tetrahedron, 24, 3655 (1968).

    Article  CAS  Google Scholar 

  71. R. Noyori, H. Takaya, Y. Nakanisi, H. Nozaki, Can. J. Chem., 47, 1242 (1969).

    Article  CAS  Google Scholar 

  72. W. R. Moser, J. Amer. Chem. Soc, 91, 1135 (1969).

    Article  CAS  Google Scholar 

  73. I. S. Lishanskii, V. I. Pomerantsev, N. G. Illarionova, A. S. Kachaturov, T. I. Vakorina, Kin. Katal., 7, l803 (1971);

    Google Scholar 

  74. I. S. Lishanskii, V. I. Pomerantsev, N. G. Illarionova, A. S. Kachaturov, T. I. Vakorina, C. A., 76, 3303 (1972).

    Google Scholar 

  75. Y. Tatsuno, A. Konishi, A. Nakamura, S. Otsuka, J. C. S. Chem. Comm., 588 (1974).

    Google Scholar 

  76. T. Aratani, Y. Yoneyoshi, T. Nagase, Tetrahedron Lett., 1707 (1975).

    Google Scholar 

  77. P. Pino et. al., in preparation.

    Google Scholar 

  78. M. Tanaka, Y. Ikeda, I. Ogata, Chem. Lett., 1115 (1975).

    Google Scholar 

  79. R. Noyori, T. Ishigami, N. Hayashi, H. Takaya, J. Amer. Chem. Soc, 95, 1674 (1973).

    Article  CAS  Google Scholar 

  80. See ref. 10, p. 30ff.

    Google Scholar 

  81. A. Stefani, D. Tatone, P. Pino, Helv. Chim. Acta, 59, 1639 (1976).

    Article  CAS  Google Scholar 

  82. G. Consiglio, unpublished results.

    Google Scholar 

  83. J. Solodar, D. O. S. 2.312.924; C. A., 80, 3672 (1974).

    Google Scholar 

  84. K. Ohkubo, K. Hirata, K. Yoshinaga, M. Okada, Chem. Lett., 183 (1976).

    Google Scholar 

  85. K. Ohkubo, K. Hirata, K. Yoshinaga, Chem. Lett., 577 (1976).

    Google Scholar 

  86. K. Ohkubo, T. Ohgushi, K. Yoshinaga, Chem. Lett., 775 (1976).

    Google Scholar 

  87. K. Ohkubo, T. Aoji, K. Hirata, K. Yoshinaga, Inorg. Nucl. Chem. Letters, 12, 837 (1976).

    Article  CAS  Google Scholar 

  88. K. Ohkubo, K. Hirata, T. Ohgushi, K. Yoshinaga, J. Coord. Chem., 6, 185 (1977).

    Article  CAS  Google Scholar 

  89. C. Carlini, D. Politi, F. Ciardelli, Chem. Comm., 1260 (l970).

    Google Scholar 

  90. G. Strukul, M. Bonivento, R. Ros, M. Graziani, Tetrahedron Lett., 1791 (1974).

    Google Scholar 

  91. G. Sbrana, G. Braca, E. Giannetti, J. C. S. Dalton, l847 (1976).

    Google Scholar 

  92. H. Aoi, M. Ishimori, S. Yoshikawa, T. Tsuruta, J. Organometal. Chem., 85, 241 (1975).

    Article  CAS  Google Scholar 

  93. H. Aoi, M. Ishimori, T. Tsuruta, Bull. Chem. Soc. Japan, 48, 1897 (1975).

    Article  CAS  Google Scholar 

  94. L. Lardicci, G. P. Giacomelli, P. Salvadori, P. Pino, J. Amer. Chem. Soc, 93, 5794 (1971).

    Article  CAS  Google Scholar 

  95. M. Ishimori, H. Aoi, T. Takeichi, T. Tsuruta, Chem. Lett., 645 (1976).

    Google Scholar 

  96. S. Yamashita, N. Yamawaki, H. Tani, Macromolecules, 6, 724 (1974).

    Article  Google Scholar 

  97. R. J. P. Corriu, J. J. E. Moreau, J. Organometal. Chem., 120, 337 (1976).

    Article  CAS  Google Scholar 

  98. K. Tamao, A. Minato, N. Miyake, T. Matsuda, Y. Kiso, M. Kumada, Chem. Lett., 133 (1975).

    Google Scholar 

  99. J. Halpern, Adv. Chem. Ser., 70, 1 (1968).

    Article  Google Scholar 

  100. H. Brunner, Angew. Chem., 83, 274 (1971).

    Article  Google Scholar 

  101. H. Brunner, Ann. N. Y. Acad. Sci., 239, 213 (1974).

    Article  CAS  Google Scholar 

  102. H. Brunner, Topics in Current Chemistry, 56, 67 (1975).

    Article  CAS  Google Scholar 

  103. K. Stanley, M. C. Baird, J. Amer. Chem. Soc., 97, 6598 (1975).

    Article  CAS  Google Scholar 

  104. H. Brunner, J. Wächter, Chem. Ber., 110, 721 (1977).

    Article  CAS  Google Scholar 

  105. W. S. Knowles, M. J. Sabacky, B. D. Vineyard, J. C. S. Chem. Comm., 10 (1972).

    Google Scholar 

  106. H. B. Kagan, T. P. Dang, J. Amer. Chem. Soc, 94, 6429 (1972).

    Article  CAS  Google Scholar 

  107. A. C. Cope, C. R. Ganellin, H. W. Johnson, Jr., T. V. Van Auken, H. J. S. Winkles, J. Amer. Chem. Soc, 85, 3276 (1963).

    Article  CAS  Google Scholar 

  108. For a review see: G. Paiaro, Organometal. Chem. Rev. A, 6, 319 (1970).

    CAS  Google Scholar 

  109. R. Lazzaroni, P. Salvadori, P. Pino, Chem. Comm., 1164 (1970).

    Google Scholar 

  110. Y. Kiso, K. Yamamoto, K. Tamao, M. Kumada, J. Amer. Chem. Soc, 94, 4373 (1972).

    Article  CAS  Google Scholar 

  111. M. Idai, H. Ishiwatari, H. Yagi, E. Tanaka, K. Onozawa, Y. Uchida, J. C. S. Chem. Coram., 170 (1975).

    Google Scholar 

  112. Y. Ohgo, S. Takeuchi, Y. Natori, J. Yoshimura, Chem. Lett., 33 (1974).

    Google Scholar 

  113. J. Furukawa, S. Akutsu, T. Saegusa, Makromol. Chem., 81, 100 (1965).

    Article  CAS  Google Scholar 

  114. T. P. Dang, J. C. Pouling, H. B. Kagan, J. Organometal. Chem., 91, 105 (1975).

    Article  Google Scholar 

  115. W. Dumont, J. C. Paulin, T. P. Dang, H. B. Kagan, J. Amer. Chem. Soc, 95, 8295 (1973).

    Article  CAS  Google Scholar 

  116. D. Y. Curtin, Record Chem. Progress, 15, 111 (1954).

    CAS  Google Scholar 

  117. G. Consiglio, Helv. Chim. Acta, 59, 124 (1976).

    Article  CAS  Google Scholar 

  118. G. Gelbard, H. B. Kagan, R. Stern, Tetrahedron, 32, 233 (1976).

    Article  CAS  Google Scholar 

  119. R. Glaser, Tetrahedron Lett., 2127 (1975).

    Google Scholar 

  120. G. Consiglio, P. Pino, in preparation.

    Google Scholar 

  121. S. Brunie, J. Mazan, N. Langlois, H. B. Kagan, J. Organometal. Chem., 114, 225 (1976).

    Article  CAS  Google Scholar 

  122. W. S. Knowles, M. J. Sabacky, B. D. Vineyard, Adv. Chem. Ser., 132, 274 (1974).

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 1977 Plenum Press, New York

About this chapter

Cite this chapter

Pino, P., Consiglio, G. (1977). Asymmetric Homogeneous Catalysis by Chiral Transition Metal Complexes. In: Tsutsui, M., Ugo, R. (eds) Fundamental Research in Homogeneous Catalysis. Springer, Boston, MA. https://doi.org/10.1007/978-1-4615-7038-7_7

Download citation

  • DOI: https://doi.org/10.1007/978-1-4615-7038-7_7

  • Publisher Name: Springer, Boston, MA

  • Print ISBN: 978-1-4615-7040-0

  • Online ISBN: 978-1-4615-7038-7

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics