Stereoselective Catalytic Reductions

  • Atta-ur-Rahman
  • Zahir Shah

Abstract

Many natural products such as amino acids, carbohydrates and nucleotides exist in living organisms predominantly in one enantiomeric form. This is the result of the remarkable ability of enzymes to affect stereoselective transformations by controlling several stereochemical aspects in single step reactions, a property which has fascinated synthetic organic chemists and triggered efforts to develop corresponding laboratory procedures for enantioselective synthesis.

Keywords

Hydride Diol Hydrazones Phosphite Silyl 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    a). J.F. Young, J.A. Osborn, F.H. Jardine, G. Wilkinson, J. Chem. Soc. Chem. Commun., 131 (1965).Google Scholar
  2. (b).
    J.A. Osborn, F.H. Jardine, G. Wilkinson, J. Chem. Soc. A, 1711 (1966).Google Scholar
  3. (c).
    J.A. Osborn, G. Wilkinson, Inorg. Synth., 10, 67 (1967).Google Scholar
  4. 2.
    For a review of Wilkinson’s catalyst, see: F.H. Jardine, Prog. Inorg. Chem., 28, 63 (1981).Google Scholar
  5. 3.
    T.P. Dang, H.B. Kagan, J. Chem. Soc. Chem. Commun., 481 (1971).Google Scholar
  6. 4.
    a). B.D. Vineyard, W.S. Knowles, M.J. Sabacky, G.L. Bachman, D.J. Weinkauff, J Amer. Chem. Soc., 99, 5946 (1977)Google Scholar
  7. (b).
    W. Vocke, R. Hänel, F.U. Flöther, Chem. Tech., 39, 123 (1987)Google Scholar
  8. (c).
    G. Parshall, W. Nugent, Chem. Tech., 18, 194 (1988)Google Scholar
  9. (d).
    G. Parshall, W. Nugent, ibid, 18, 376 (1988).Google Scholar
  10. 5.
    T.P. Dang, H.B. Kagan, J Amer. Chem. Soc., 94, 6429 (1972).Google Scholar
  11. 6.
    L. Horner, H. Seigel, H. Buthe, Angew. Chem., 7, 9420 (1968).Google Scholar
  12. 7.
    G.D. Melillo, R.D. Larsen, DJ. Mathre, W.F. Shukis, A.W. Wood, J.R. Colleluori, J. Org. Chem. 52, 5143 (1987).Google Scholar
  13. 8.
    a). H. Parnes, EJ. Shelton, Int. J. Pept. Protein Res., 27, 239 (1986)Google Scholar
  14. (b).
    H. Parnes, E J. Shelton, G.T. Huang, ibid, 28, 403 (1986).Google Scholar
  15. (c).
    H. Parnes, E.J. Shelton, Synth. Appl. Isot. Labeled Comp. Proc. Int. Symp. 2nd. 1985, P 159 (pub. 1986 ).Google Scholar
  16. 9.
    D.P. Riley, P.E. Shumate, J. Org. Chem. 45, 5187 (1980).Google Scholar
  17. 10.
    R.B. King, J. Bakos, C.D. Hoff, L. Marko, J. Org. Chem. 44, 1729 (1979).Google Scholar
  18. 11.
    M.D. Fryzuk, B. Bosnich, J. Amer. Chem. Soc., 99, 6262 (1977).Google Scholar
  19. 12.
    a) S.B. Wilde, N.K. Roberts, J. Amer. Chem. Soc., 101, 6254 (1979)Google Scholar
  20. (b).
    M.D. Fryzuk, B. Bosnich, J Amer. Chem. Soc., 100, 5491 (1978).Google Scholar
  21. 13.
    a). T. Hayashi, M. Kumada, Acc. Chem. Res., 15, 395 (1982)Google Scholar
  22. (b).
    H.B. Kagan, J.C. Fiaud, C.H. Hoornaert, D. Meyer, J.C. Poulin, Bull. Soc. Chim. Belg., 88, 923 (1979).Google Scholar
  23. 14.
    W. Bergstein, A. Kleemann, J. Martins, Synthesis, 76 (1981).Google Scholar
  24. 15.
    C.F. Hobbs, W.S. Knowles, J. Org. Chem., 46, 4422 (1981).Google Scholar
  25. 16.
    J.D. Morrison, W.F. Masler, J. Org. Chem., 39, 270 (1974).Google Scholar
  26. 17.
    J.D. Morrison, W.F. Masler, M.K. Neuberg, Adv. Catal., 25, 81 (1976).Google Scholar
  27. 18.
    R. Glaser, J. Blumenfeld, M. Twaik, Tetrahedron Lett., 52, 4639 (1977).Google Scholar
  28. 19.
    R. Glaser, S. Geresh, J. Blumenfeld, M. Twaik, Tetrahedron, 34, 2405 (1978).Google Scholar
  29. 20.
    P. Aviron-Violet, Y. Collenille, J. Varagnal, J. Mol. Catal., 5, 41 (1979).Google Scholar
  30. 21.
    T.P. Dang, J.C. Poulin, H.B. Kagan, J. Organomet. Chem., 91, 105 (1975).Google Scholar
  31. 22.
    a) D.L. Allen, V.C. Gibson, M.H.L. Green, J.F. Skinner, J. Bashkin, P.D. Grebenik, J. Chem. Soc. Chem. Commun., 895 (1983)Google Scholar
  32. (b).
    I. Ojima, N. Noyoda, Tetrahedron Lett., 21, 1051 (1980).Google Scholar
  33. 23.
    K. Achiwa, J. Amer. Chem. Soc., 98, 8265 (1976).Google Scholar
  34. 24.
    T. Hayashi, K. Yamamoto, M. Kumada, Tetrahedron Lett., 4405 (1974).Google Scholar
  35. 25.
    T. Hayashi, T. Mise, M. Kumada, Tetrahedron Lett., 4351 (1976).Google Scholar
  36. 26.
    A. Miijashita, A. Yasuda, H. Takaya, K. Toriumi, T. Ito, T. Souchi, R.N. Noyori, J. Amer. Chem. Soc., 102, 7932 (1980).Google Scholar
  37. 27.
    M. Tanaka, I. Ogata, J. Chem. Soc. Chem. Commun., 735 (1975).Google Scholar
  38. 28.
    R.B. King, J. Bakos, C.D. Hoff, L. Marko, J. Org. Chem., 44, 3095 (1979).Google Scholar
  39. 29.
    S.Y. Zhang, S. Yemul, H.B. Kagan, R.Stern, D. Commereuc, Y. Chauvin, Tetrahedron Lett., 3955 (1981).Google Scholar
  40. 30.
    (a) J.M. Brown, P.A. Chaloner, G.A. Morris, J. Chem. Soc. Perkin, Trans. II, 1583 (1987)Google Scholar
  41. (b).
    J. Halpern, C.R. Landis, J. Amer. Chem. Soc., 109, 1746 (1987).Google Scholar
  42. 31.
    J.M. Brown, P.L. Evans, Tetrahedron, 44, 4905 (1988).Google Scholar
  43. 32.
    (a) J. Halpern, Adv. in Catalysis, 11, 301 p.73 (1959)Google Scholar
  44. (b).
    J. Halpern, R.S. Nyholm, Proc. 3rd. lnt. Cong. Catal., (W.M.H. Sachter, G.C.A. Schuitt, P. Zwietering, eds.) Vol.I, North Holland Pub. Co., Amsterdam, P.25, 146 (1965)Google Scholar
  45. (c).
    M.F. Sloane, A.S. Matlack, D.S. Breslow, J. Amer. Chem. Soc., 85, 4014 (1963).Google Scholar
  46. 33.
    a). G. Consiglio, P. Pino, Top. Curr. Chem., 105, 77 (1982)Google Scholar
  47. (b).
    G. Consiglio, P. Pino, Adv. Chem. Ser., 196, 371 (1982).Google Scholar
  48. 34.
    T. Hayashi, N. Kawamura, Y. Ito, J. Amer. Chem. Soc., 109, 7876 (1987).Google Scholar
  49. 35.
    J.M. Brown, A.P. James, J. Chem. Soc. Chem. Commun., 181 (1987).Google Scholar
  50. 36.
    A.S.C. Chua, J.J. Pluth, J. Halpern, J. Amer. Chem. Soc., 102, 5952 (1980).Google Scholar
  51. 37.
    a) A.S.C. Chan, J.J. Pluth, J. Halpern, Inorg. Chim. Acta, 37, 1477 (1979)Google Scholar
  52. (b).
    N.W. Alcock, J.M. Brown, A.E. Derome, A.R. Lucy, J. Chem. Soc. Chem. Commun., 575 (1985)Google Scholar
  53. (c).
    N.W. Alcock, J.M. Brown, P. J. Maddox, ibid, 1532 (1986).Google Scholar
  54. 38.
    R. Selke, H. Pracejus, J. Mol. Catal., 38, 213 (1986).Google Scholar
  55. 39.
    T. Ikariya, Y. Ishii, H. Kawano, T. Arai, M. Saburi, S. Yoshikawa, S. Akutagawa, J. Chem. Soc. Chem. Commun., 922 (1985).Google Scholar
  56. 40.
    H. Takahashi, K. Achiwa, Chemistry Lett., 1921 (1987).Google Scholar
  57. 41.
    H. Takaya, T. Ohta, N.Sayo, H. Kumobayashi, S. Akutagawa, S. Inoue, I. Kasahara, R. Noyori, J. Amer. Chem. Soc., 109, 1596 (1987).Google Scholar
  58. 42.
    T. Ohta, H. Takaya, M. Kitamura, K. Nagai, R. Noyori, J. Org. Chem., 52, 3174 (1987).Google Scholar
  59. 43.
    H. Kawano, Y. Ishii, T. Ikariya, M. Saburi, S. Yoshikawa, Y.Uchida, H. Kumobayashi, Tetrahedron Lett., 28, 1905 (1987).Google Scholar
  60. 44.
    a) W.C. Christopfel, B.D. Vineyard, J. Amer. Chem. Soc., 101, 4406 (1979)Google Scholar
  61. (b).
    W.S. Knowles, Acc. Chem. Res., 16, 106 (1983).Google Scholar
  62. 45.
    M.Kitamura, T. Ohkuma, S. Inoue, N. Sayo, H. Kumobayashi, S. Akutagawa, T. Ohta, H. Takaya, R. Noyori, J. Amer. Chem. Soc., 110, 629 (1988).Google Scholar
  63. 46.
    R. Noyori, M. Ohta, Y. Hsiao, M. Kitamura, J. Amer. Chem. Soc., 108, 7117 (1986).Google Scholar
  64. 47.
    M. Kitamura, Y. Hsiao, R. Noyori, Tetrahedron Lett., 28, 4829 (1987).Google Scholar
  65. 48.
    E. Cesarotti, R. Ugo, H.B. Kagan, Angew. Chem., 18, 779 (1979).Google Scholar
  66. 49.
    E. Cesarotti, H.B. Kagan, R. Goddard, C. Krüger, J. Organomet. Chem., 162, 297 (1978).Google Scholar
  67. 50.
    R. Stern, L.Sajas, Tetrahedron Lett., 6313 (1968).Google Scholar
  68. 51.
    a) Y. Ohgo, S. Takeuchi, J.Yoshimura, Bull. Chem. Soc. Jpn., 43, 505 (1970)Google Scholar
  69. (b).
    Y. Ohgo, S. Takeuchi, J.Yoshimura, ibid, 44, 283 (1971).Google Scholar
  70. 52.
    Y. Ohgo, K. Kobayashi, S. Takeuchi, Y. Yoshimura, ibid, 45, 933 (1972).Google Scholar
  71. 53.
    S. Takeuchi, Y. Ohgo, ibid, 54, 2136 (1981).Google Scholar
  72. 54.
    A. Fischli, D. Süss, Helv. Chim. Acta, 62, 2361 (1979).Google Scholar
  73. 55.
    A. Fischli, J. J. Daly, ibid, 63, 1628 (1980).Google Scholar
  74. 56.
    A. Fischli, P.M. Müller, Helv. Chim. Acta, 63, 529 (1980)Google Scholar
  75. 57.
    A. Fischli, P.M. Müller, Helv. Chim. Acta, 63, 1619 (1980).Google Scholar
  76. 58.
    H. Brunner, J. Wächter, J. Schmidbauer, G.M. Sheldrick, P.G. Jones, Angew. Chem., 25, 371 (1986).Google Scholar
  77. 59.
    B.D. Zwick, A.M. Arif, A.T. Patton, J.A. Gladysz, ibid, 26, 910 (1987).Google Scholar
  78. 60.
    I. Ojima, T. Kogure, Rev. Silicon, Germanium, Tin Lead Compds., 5, 7 (1980).Google Scholar
  79. 61.
    I. Ojima, K. Yamamoto, M. Kumada, in: “Aspects of Homogeneous Catalysis”, (R. Ugo, ed.), Vol.3, PP 185, D. Reidel, Dordrecht (1977).Google Scholar
  80. 62.
    a) K. Yamamoto, T. Hayashi, M. Zembayashi, M. Kumada, J. Organomet. Chem., 118, 161 (1976)Google Scholar
  81. (b).
    K. Yamamoto, T Hayashi, M. Kumada, J. Amer. Chem. Soc., 93, 5301 (1971).Google Scholar
  82. 63.
    a). K. Yamamoto, T. Hayashi, Y. Uramoto, R. Ito, M. Kumada, J. Organomot. Chem., 118, 331 (1976)Google Scholar
  83. (b).
    K. Yamamoto, Y. Uramoto, M. Kumada, ibid, 31, C9 (1971).Google Scholar
  84. 64.
    T. Hayashi, K. Tamao, Y. Katsuro, I. Nakae, M. Kumada, Tetrahedron Lett., 21, 1871 (1980).Google Scholar
  85. 65.
    Y.Kiso, K. Yamamoto, K. Tamao, M. Kumada, J. Amer. Chem. Soc., 94, 4373 (1972).Google Scholar
  86. 66.
    L.H. Sommer, J.E. Lyons, H. Fujimoto, J. Amer. Chem. Soc., 91, 7051 (1969).Google Scholar
  87. 67.
    A.J. Chalk, J.F. Harrod, J. Amer. Chem. Soc., 87, 16 (1965).Google Scholar
  88. 68.
    For a review, see: G. Paiaro, Organomet. Chem. Rev. Sect. A, 6, 319 (1970).Google Scholar
  89. 69.
    I. Ojima, T.Kogure, Y. Nagai, Tetrahedron Lett., 2415 (1973).Google Scholar
  90. 70.
    M. Fieser, L.F. Fieser, in: “Reagents for Organic Synthesis” Vol.5, pp. 739, Wiley, New York (1975).Google Scholar
  91. 71.
    I. Ojima, T. Kogure, Tetrahedron Lett., 4865 (1973).Google Scholar
  92. 72.
    H.B. Kagan, N. Langlois, T.-P. Dang, J. Organomet. Chem., 90, 353 (1975).Google Scholar
  93. 73.
    G. Zassinovich, C. Del Bianco, G. Mestroni, J. Organomet. Chem., 197, 85 (1980).Google Scholar
  94. 74.
    K. Osakada, M. Obona, T. Ihariya, M. Saburi, S. Yushikawa, Tetrahedron Lett., 4297 (1981).Google Scholar
  95. 75.
    P. Bonvicini, A. Levi, G. Modena, G. Scorrano, J. Chem. Soc. Chem. Commun., 1188 (1972).Google Scholar
  96. 76.
    a) I. Ojima, T. Kogure, J. Chem. Soc. Chem. Commun., 428 (1977)Google Scholar
  97. (b).
    R.R. Shrock, J.A. Osborn, ibid, 567 (1970).Google Scholar
  98. 77.
    T. Hayashi, K. Kanehira, M. Kumada, Tetrahedron Lett., 4417 (1981).Google Scholar
  99. 78.
    J. Solodar, Chem. Tech., 421 (1975).Google Scholar
  100. 79.
    D. Wang, T.H. Chau, Tetrahedron Lett., 24 (15), 1573 (1983).Google Scholar
  101. 80.
    I. Ojima, T. Kogure, T. Terasaki, K. Achiwa, J. Org. Chem., 43, 3444 (1978).Google Scholar
  102. 81.
    a) M. Parko, W.O. Nelson, W.A. Wood, J. Biol. Chem. 207, 51 (1954)Google Scholar
  103. (b).
    G.M. Brown, J.J. Reynolds, Ann. Rev. Biochem., 32, 419 (1963).Google Scholar
  104. 82.
    T. Tanis, in: “Organometallics” (H. Nocaki, H. Yamamoto, J. Tsuji, R. Noyori, eds.), Kagakuzokan 105, 121 Kagakudojin (Japan) (1985).Google Scholar
  105. 83.
    K. Tani, E. Tanigawa, Y. Tatsuro, S. Otsuka, Chemistry Lett., 737 (1986).Google Scholar
  106. 84.
    a) S. Masamune, W. Choy, J.S. Petersen, R.L.R. Sita, Angew. Chem., 24, 1 (1985)Google Scholar
  107. (b).
    K. Yamamoto, S.U. Rahman, Chemistry Lett., 1603 (1984).Google Scholar
  108. 85.
    a) J.F. Deuble, C.McGettigan, J.M. Stryker, Tetrahedron Lett., 31, 2397 (1990)Google Scholar
  109. (b).
    W.S. Mahoney, J.M. Stryker, J. Amer. Chem. Soc., 111, 8818 (1989)Google Scholar
  110. (c).
    T. M. Koenig, J.F. Deuble, D.M. Brestensky, J.M. Stryker, Tetrahedron Lett., 30, 5677 (1989).Google Scholar
  111. (d).
    W.S. Mahoney, D.M. Brestensky, J. M. Stryker, J. Amer. Chem. Soc., 110, 291 (1988)Google Scholar
  112. (e).
    K. Yamamoto, T. Hayashi, M. Kumada, J. Organomet. Chem., 46, C65 (1972)Google Scholar
  113. (f).
    T. Hayashi, K. Yamamoto, M. Kumada, J. Organomet. Chem., 112, 253 (1976).Google Scholar
  114. 86.
    a). T. Hayashi, K. Yamamoto, K. Kasuga, H. Omizu, M. Kumada, J. Organomet. Chem., 113, 127 (1976).Google Scholar
  115. 87.
    K. Yamamoto, T. Hayashi, M. Kumada, ibid, 54, C45 (1973).Google Scholar
  116. 88.
    I. Ojima, T. Kogure; M. Kumagai, S. Horiuchi, T. Sato, ibid, 122, 83 (1976).Google Scholar
  117. 89.
    a). H.Brunner, G. Riepl, Angew. Chem., 21, 377 (1982).Google Scholar
  118. 90.
    A. Kinting, H.J. Kreuzfeld, H.P. Abicht, J. Organomet. Chem., 370, 343 (1989).Google Scholar
  119. 91.
    W. Dumont, J.-C. Poulin, T. P. Dang, H.B. Kagan, J. Amer. Chem. Soc., 95, 8295 (1973).Google Scholar
  120. 92.
    a) R.J.P. Corriu, J.J.E. Moreau, J. Organomet. Chem., 85, 19 (1975).Google Scholar
  121. (b).
    R.J.P. Corriu, J.J. E. Moreau, ibid, 64, C51 (1974).Google Scholar
  122. 93.
    I. Kolb, M. Cerny, J. Hetflejs, React. Kinet. Catal. Lett., 7, 199 (1977).Google Scholar
  123. 94.
    T. Hayashi, T. Mise, M. Fukushima, M. Kagotani, N. Nagashima, Y. Hamada, A. Matsumoto, S. Kawakami, M. Konishi, K. Yamamoto, M. Kumada, Bull. Chem. Soc. Jpn. 53, 1138 (1980).Google Scholar
  124. 95.
    I. Ojima, T. Kogure, M. Kumagai, J. Org. Chem., 42, 1671 (1977).Google Scholar
  125. 96.
    R. Glaser, Tetrahedron Lett., 2127 (1975).Google Scholar
  126. 97.
    a) G. Vavon, A. Antonini, C.R. Acad. Sci., 230, 1870 (1950)Google Scholar
  127. (b).
    G. Vavon, A. Antonini, ibid, 232, 1120 (1951).Google Scholar
  128. 98.
    I. Ojima, T. Tanaka, T. Kogure, Chemistry Lett., 823 (1981).Google Scholar
  129. 99.
    Y. Amrani, D. Sinou, J. Mol. Catal., 24, 231 (1984).Google Scholar
  130. 100.
    D. Sinou, Y. Amrani, J. Mol. Catal., 36, 319, (1986).Google Scholar
  131. 101.
    T.P. Dang, J. Jenck, D. Morel, (Rhone-Poulenc), Eur. Pat. Appl. Ep. 133, 127A1 (1985).Google Scholar
  132. 102.
    F. Alario, Y. Amrani, Y. Colleuille, T.P. Dang, J. Jenck, D. Morel, D. Sinou, J. Chem. Soc. Chem. Commun., 203 (1986).Google Scholar
  133. 103.
    R. Benhanza, Y. Amrani, D. Sinou, J. Organomet. Chem., 288, C37 (1985).Google Scholar
  134. 104.
    a) T. Harada, Y. Izumi, Chemistry Lett., 1195 (1978)Google Scholar
  135. (b).
    A. Tai, M. Nakahata, T. Harada, Y. Izumi, ibid, 1125 (1980).Google Scholar
  136. 105.
    a) T. Osawa, T. Harada, Bull. Chem. Soc. Jpn., 57, 1518 (1984)Google Scholar
  137. (b).
    A.Tai, T. Harada, Y. Hiraki, S. Murakami, ibid, 56, 1414 (1983)Google Scholar
  138. (c).
    S. Murakami, T. Harada, A. Tai, ibid, 53, 1356 (1980).Google Scholar
  139. 106.
    (a) Y. Hiraki, K. Ito, T. Harada, A. Tai, Chemistry Lett, 131 (1981).Google Scholar
  140. 107.
    a) A. Tai, K. Ito, T. Harada, Bull. Chem. Soc. Jpn., 54, 223 (1981).Google Scholar
  141. (b).
    A. Tai, H. Watanabe, T. Harada, ibid, 52, 1468 (1979).Google Scholar
  142. 108.
    E.I. Klabunovskii, Izv. Akad. Nauk SSSR, Ser. Khim., 505 (1984).Google Scholar
  143. 109.
    K. Ito, T. Harada, A. Tai., Bull. Chem. Soc. Jpn., 53, 3367 (1980).Google Scholar
  144. 110.
    M. Nakahata, M. Imaida, H. Ozaki, T. Harada, A. Tai, Bull. Chem. Soc. Jpn., 55, 2186 (1982).Google Scholar
  145. 111.
    M. Bartok, Gy. Wittman, Gy. Göndös, G.V. Smith, J. Org. Chem., 52, 1139 (1987).Google Scholar
  146. 112.
    A. Hatta, W. Suetaka, Bull. Chem. Soc. Jpn., 48, 2428 (1975).Google Scholar
  147. 113.
    A. Kumobatsu, S. Komatsu, “Raney Shokubai”, Kyoritsushuppan Co., Tokoyo (1971).Google Scholar
  148. 114.
    H.W. Krause, React. Kinet. Catal. Lett., 10, 243 (1979).Google Scholar
  149. 115.
    a) K. Ohkubo, H. Fujimori, K. Yoshinaga, Inorg.Nucl. Chem.Lett., 15, 231 (1979)Google Scholar
  150. (b).
    K. Ohkubo, M. Haga, K. Yoshinaga, Y. Motazato, ibid, 17, 215 (1981).Google Scholar
  151. 116.
    N. Takaishi, H. Imai, C.A. Bertelo, J.K. Stille, J. Amer. Chem. Soc., 100, 264, 268 (1978).Google Scholar
  152. 117.
    K. Achiwa, Heterocycles, 9, 1539 (1978).Google Scholar
  153. 118.
    K. Achiwa, Chemistry Lett., 905 (1978).Google Scholar
  154. 119.
    U. Nagel, H. Menzel, P.W. Lednor, W. Beck, A. Guyot, M. Barholin, Nature, 36, 578 (1981).Google Scholar
  155. 120.
    G.L. Baker, S J. Fritschel, J.R. Stille, J.K. Stille, J. Org. Chem., 46, 2954 (1981).Google Scholar
  156. 121.
    a) A. Pedrazzoli, Helv. Chem. Acta, 40, 80 (1957)Google Scholar
  157. (b).
    A. Pedrazzoli, Chimica, 10, 260 (1956).Google Scholar
  158. 122.
    M. Takasaki, K. Harada, Chemistry Lett., 1745 (1984).Google Scholar
  159. 123.
    a) K.Harada, M. Takasaki, Bull. Chem. Soc. Jpn., 57, 1427 (1984).Google Scholar
  160. (b).
    M. Tamura, K. Harada, ibid, 53, 561 (1980).Google Scholar
  161. 124.
    S. Yamada, T. Shioiri, T. Fuji, Chem. Pharm. Bull., 10, 688 (1962).Google Scholar
  162. 125.
    J.C. Sheehan, R.E. Chandler, J. Amer. Chem. Soc., 83, 4795 (1961).Google Scholar
  163. 126.
    J.P. Vigneron, H.B. Kagan, H. Horeau, Tetrahedron Lett., 5681 (1968).Google Scholar
  164. 127.
    J.S. Davies, M.C. Eaton, M.N. Ibrahim, J. Heterocyc. Chem., 17, 1813 (1980).Google Scholar
  165. 128.
    M. Nakayama, G. Maeda, T. Kancko, H. Katsura, Bull. Chem, Soc. Jpn., 44, 1150 (1971).Google Scholar
  166. 129.
    D. Valentine, Jr., J.W. Scott, Synthesis, 329 (1978).Google Scholar
  167. 130.
    V. Prelog, Helv. Chim. Acta, 36, 308 (1953).Google Scholar
  168. 131.
    V. Prelog, Bull. Soc. Chim. Franee, 987 (1956).Google Scholar
  169. 132.
    E.E. Eliel, in: “Asymmetric Synthesis” (J.D. Morrison, ed.), Vol.2, PP.125–155. Academic Press New York (1983).Google Scholar
  170. 133.
    T. Ueno, T. Nakashima, Y. Hayashi, H. Fukami, Agric. Biol. Chem., 39, 1115 (1975).Google Scholar
  171. 134.
    N. Izumiya, S. Lee, T. Kanmera, H. Aoyagi, J. Amer. Chem. Soc., 99, 8346 (1977).Google Scholar
  172. 135.
    W.L. Meyer, L.F. Kuyper, R.B. Lewis, G.E. Templeton, S.H. Woodhead, Biochem. Biophys. Res. Commun., 56, 234 (1974).Google Scholar
  173. 136.
    H. Poisel, U. Schmidt, Chem. Ber., 106, 3408 (1973).Google Scholar
  174. 137.
    B.W. Bycroft, G.R. Lee., J. Chem. Soc. Chem. Commun., 988 (1975).Google Scholar
  175. 138.
    E J. Corey, H.S. Sachdev, J.Z. Gougoutas, W. Saenger, J. Amer. Chem. Soc., 92, 2488 (1970).Google Scholar
  176. 139.
    S. Akabori, T. Ikenaka, K. Matsumoto, Nippon Kagaku Zasshi, 73, 112 (1952).Google Scholar
  177. 140.
    S. Mitsui, T. Kamaishi, T. Imaizumi, I. Takamura, Nippon Kagaku Zasshi, 83, 1115 (1962).Google Scholar
  178. 141.
    T. Kamaishi, S. Mitsui, ibid, 86, 623 (1965).Google Scholar
  179. 142.
    M. Kawana, S. Emoto, Bull. Chem. Soc. Jpn., 41, 259 (1968).Google Scholar
  180. 143.
    A. Mckenzie, E.W. Christie, Biochem.Z., 177, 426 (1935).Google Scholar
  181. 144.
    M.M. Jamison, E.E. Turner, J. Chem. Soc., 538 (1941).Google Scholar
  182. 145.
    E.E. Turner, M.M. Harris, Quart.Revs. (London). 1, 299 (1974).Google Scholar
  183. 146.
    S. Mitsui, M. Kanai, Nippon Kagaku Zasshi, 87, 179 (1966).Google Scholar
  184. 147.
    K. Harada, T. Munegumi, S. Nomoto, Tetrahedron Lett., 22, 111 (1981).Google Scholar
  185. 148.
    S. Mitsui, A. Kanei, Nippon Kagaku Zasshi, 86, 627 (1965).Google Scholar
  186. 149.
    K. Harada, T. Munegumi, Bull. Chem. Soc. Jpn., 56, 2774 (1983).Google Scholar
  187. 150.
    K. Harada, T. Munegumi, ibid, 57, 3203 (1984).Google Scholar
  188. 151.
    K. Harada, K. Matsumoto, J. Org. Chem., 33, 4467 (1968).Google Scholar
  189. 152.
    a) K. Harada, K. Katsumoto, J. Org. Chem., 32, 1794 (1967)Google Scholar
  190. (b).
    K. Harada, ibid, 32, 1790 (1967).Google Scholar
  191. 153.
    A. Kanai, S. Mitsui, Nippon Kagaku Zasshi, 87, 183 (1966).Google Scholar
  192. 154.
    R.G. Hiskey, R.C. Northrop, J. Amer. Chem. Soc., 83, 4798 (1961).Google Scholar
  193. 155.
    R.G. Hiskey, R.C. Northrop, ibid, 87, 1753 (1965).Google Scholar
  194. 156.
    S. Yamada, S. Hashimoto, Tetrahedron Lett., 997 (1976).Google Scholar
  195. 157.
    S. Yamada, N. Ikota, K. Achiwa, Tetrahedron Lett., 1001 (1976).Google Scholar
  196. 158.
    K. Harada, T. Yoshida, J. Org. Chem., 37, 4366 (1972).Google Scholar
  197. 159.
    I. Miyazawa, K. Takashima, T. Yamada, S. Kuwata, H. Watanabe, Bull. Chem. Soc. Jpn., 55, 341 (1982).Google Scholar
  198. 160.
    K. Harada, S. Shiono, ibid., 57, 1367 (1984).Google Scholar
  199. 161.
    K. Kuzuhara, T. Komatsu, E. Emoto, Tetrahedron Lett., 3563 (1978).Google Scholar
  200. 162.
    Y. Tachibana, M. Ando, H. Kuzuhara, Chemistry Lett., 1769 (1982).Google Scholar
  201. 163.
    Y. Tachibana, M. Ando, H. Kuzuhara, Bull. Chem. Soc. Jpn., 56, 3652 (1983).Google Scholar
  202. 164.
    K. Bernauer, R. Deschenaux, T. Taura, Helv. Chim. Acta, 66, 2049 (1983).Google Scholar
  203. 165.
    K. Matsumoto, K. Harada, J. Org. Chem., 31, 1956 (1966).Google Scholar
  204. 166.
    K. Harada, T. Yoshida, Bull. Chem. Soc. Jpn., 43, 921 (1970).Google Scholar
  205. 167.
    K. Harada, S. Shiono, ibid, 57, 1040 (1984).Google Scholar
  206. 168.
    K. Harada, T. Yoshida, J. Chem. Soc. Chem. Commun., 1071 (1970).Google Scholar
  207. 169.
    S. Kiyooka, K. Takeshima, H. Yamamoto, K. Suzuki, Bull. Chem. Soc. Jpn., 49, 1897 (1976).Google Scholar
  208. 170.
    K. Harada, Y. Kataoka, Tetrahedron Lett. 2103 (1978).Google Scholar
  209. 171.
    W.H. Pirkle, J.R. Hanske, J. Org. Chem., 42, 2436 (1977).Google Scholar
  210. 172.
    K. Harada, T. Iwasaki, T. Okawara, Bull. Chem. Soc. Jpn., 46, 1901 (1973).Google Scholar
  211. 173.
    D.E. Nichols, C.F. Barfknecht, D.B. Rusterholz, J. Med. Chem., 16, 480 (1973).Google Scholar
  212. 174.
    K. Harada, M. Tamura, Bull. Chem. Soc. Jpn., 52, 1227 (1979).Google Scholar

Copyright information

© Springer-Verlag New York, Inc. 1993

Authors and Affiliations

  • Atta-ur-Rahman
    • 1
  • Zahir Shah
    • 1
  1. 1.H.E.J. Research Institute of ChemistryUniversity of KarachiKarachiPakistan

Personalised recommendations