Skip to main content

Organotitanium reagents in organic synthesis a simple means to adjust reactivity and selectivity of carbanions

  • Conference paper
  • First Online:
Synthetic and Structural Problems

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 106))

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

Access this chapter

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Abbreviations

Me:

methyl

Et:

ethyl

Pr:

n-propyl

iPr:

isopropyl

Bu:

n-butyl

Ph:

phenyl

Cp:

η5-cyclopentadienyl

M:

metal

I. References

  1. Segnitz, A.: in Houben-Weyl-Müller, Methoden der Organischen Chemie, Vol. 13/7, p. 263, Stuttgart, Thieme Verlag 1975

    Google Scholar 

  2. Gmelin Handb., Titanorganische Verbindungen, Vol. 40, N.Y. 1977

    Google Scholar 

  3. Sinn, H., Kaminsky, W.: Adv. Organomet. Chem. 18, 99 (1980)

    Google Scholar 

  4. Pino, P., Mülhaupt, R.: Angew. Chem. 92, 869 (1980); Angew. Chem. Int. Ed. Engl. 19, 857 (1980)

    Google Scholar 

  5. Chatt, J., Delworth, J. R., Richards, R. L.: Chem. Rev. 78, 589 (1978)

    Google Scholar 

  6. Fachinetti, G., Floriani, C.: J. Organomet. Chem. 71, C5 (1974)

    Google Scholar 

  7. McDermott, J. X., Whitesides, G. M.: J. Am. Chem. Soc. 96, 947 (1974)

    Google Scholar 

  8. Fachinetti, G. et al.: J. Chem. Soc., Dalton Trans. 1977, 2297

    Google Scholar 

  9. Shoer, L. J., Schwartz, J.: J. Am. Chem. Soc. 99, 5832 (1977)

    Google Scholar 

  10. Klei, B., Teuber, J. H., de Liefde Meijer, H. J.: Chem. Comm. 1981, 342

    Google Scholar 

  11. Dormond, A. et al.: J. Organomet. Chem. 177, 181 (1979)

    Google Scholar 

  12. Lee, J. B. et al.: J. Am. Chem. Soc. 103, 7358 (1981); and lit. cited therein

    Google Scholar 

  13. Kano, S. et al.: Synthesis 1980, 695, 741

    Google Scholar 

  14. Colomer, E., Corriu, R.: J. Organomet. Chem. 21, 381 (1970)

    Google Scholar 

  15. Neese, H. J., Bürger, H.: J. Organomet. Chem. 32, 213

    Google Scholar 

  16. Schwartz, J.: Angew. Chem. 88, 402 (1976); Angew. Chem., Int. Ed. Engl. 15, 333 (1976)

    Google Scholar 

  17. Ashby, E. C., Noding, S. A.: J. Org. Chem. 45, 1035 (1980)

    Google Scholar 

  18. Sato, F. et al.: Chem. Lett. 1980, 99

    Google Scholar 

  19. Coleman, R. A. et al.: J. Organomet. Chem. 146, 221 (1978)

    Google Scholar 

  20. Eisch, J. J., Galle, J. E.: J. Organomet. Chem. 160, C8 (1978)

    Google Scholar 

  21. Carr, D. B., Schwartz, J.: J. Am. Chem. Soc. 101, 3521 (1979)

    Google Scholar 

  22. Bogdanovic, B. et al.: Angew. Chem. 94, 206 (1982); Angew. Chem., Int. Ed. Engl. 21, 199 (1982); Angew. Chem. Suppl. 1982, 457–470

    Google Scholar 

  23. Fell, B., Asinger, F., Sulzbach, R. A.: Chem. Ber. 103, 3830 (1970)

    Google Scholar 

  24. Review: a) Negishi, E.: Pure Appl. Chem. 53, 2333 (1981)

    Google Scholar 

  25. Brown, D. C. et al.: J. Org. Chem. 44, 3457 (1979)

    Google Scholar 

  26. Schiavelli, M. D., et al.: J. Org. Chem. 46, 807 (1981)

    Google Scholar 

  27. Wilke, G.: J. Organomet. Chem. 200, 349 (1980)

    Google Scholar 

  28. Yoshida, T.: Chem. Lett. 1982, 293

    Google Scholar 

  29. Pez, G. P., Armor, J. N.: Adv. Organomet. Chem. 19, 2 (1981)

    Google Scholar 

  30. McMurry, J. E.: Acc. Chem. Res. 7, 281 (1974)

    Google Scholar 

  31. review of reductions using other lowvalent Ti compounds: Castedo, L. et al.: J. Org. Chem. 46, 4292 (1981) and lit. cited therein

    Google Scholar 

  32. Rieke, R. D.: Acc. Chem. Res. 10, 301 (1977)

    Google Scholar 

  33. Mukaiyama, T.: Angew. Chem. 89, 858 (1977); Angew. Chem., Int. Ed. Engl. 16, 817 (1977)

    Google Scholar 

  34. Reetz, M. T.: Angew. Chem. 94, 97 (1982); Angew. Chem., Int. Ed. Engl. 21, 96 (1982)

    Google Scholar 

  35. Chan, T. H., Fleming, I.: Synthesis 1979, 761

    Google Scholar 

  36. See for example: Chem. Abstr. 61: 4223f (1964); 67: 73173b (1967); 74: 100452v (1971)

    Google Scholar 

  37. Seebach, D. et al.: Synthesis 1982, 138

    Google Scholar 

  38. „Titansäureester“, Information Pamphlet, Dynamit Nobel AG, Troisdorf, W-Germany

    Google Scholar 

  39. Katsuki, T., Sharpless, K. B.: J. Am. Chem. Soc. 102, 5974 (1980)

    Article  Google Scholar 

  40. Labinger, J. A.: J. Organomet. Chem. 227, 341 (1982)

    Google Scholar 

  41. Labinger, J. A.: J. Organomet. Chem. 196, 37 (1980)

    Google Scholar 

  42. Labinger, J. A.: J. Organomet. Chem. 180, 187 (1979)

    Google Scholar 

  43. Labinger, J. A.: J. Organomet. Chem. 167, 19 (1979)

    Google Scholar 

  44. Clark, R. J. H., Moorhouse, S., Stockwell, J. A.: Organomet. Chem. Rev., Vol. III, p. 223, ((ed.) Seyferth, D.), 1977

    Google Scholar 

  45. Clark, R. J. H.: Comprehensive Inorganic Chem., Vol. III, p. 355, Oxford, Pergamon Press 1973

    Google Scholar 

  46. Feld, G., Cowe, P. L.: The Organic Chemistry of Titanium, London, Butterworths 1965

    Google Scholar 

  47. Clark, R. J. H.: The Chemistry of Titanium and Vanadium, Amsterdam, Elsevier 1968

    Google Scholar 

  48. Kepert, D. L.: The Early Transition Metals, N.Y., Academic Press 1972

    Google Scholar 

  49. Wailes, P. C., Coutts, R. S. P., Weigold, H.: Organometallic Chemistry of Titanium, Zirconium and Hafnium, N.Y., Academic Press 1974

    Google Scholar 

  50. Stowell, J. C.: Carbanions in Organic Synthesis, N.Y., Wiley 1979

    Google Scholar 

  51. Reetz, M. T. et al.: Chem. Industry 1981, 541

    Google Scholar 

  52. Wenderoth, B.: Diplomarbeit, Univ. Marburg 1980

    Google Scholar 

  53. Reetz, M. T.: Nachr. Chem. Lab. Techn. 29, 165 (1981)

    Google Scholar 

  54. Dijkgraaf, C., Rousseau, J. P. G.: Spectrochim Acta, A, 24, 1213 (1968)

    Google Scholar 

  55. Westermann, J.: projected Dissertation, Univ. Marburg

    Google Scholar 

  56. Reetz, M. T., Peter, R.: Tetrahedron Lett. 1981, 4691

    Google Scholar 

  57. Wilkinson, G.: Pure Appl. Chem. 30, 627 (1972)

    Google Scholar 

  58. Davidson, P. J., Lappert, M. F., Pearce, R.: Chem. Rev. 76, 219 (1976)

    Google Scholar 

  59. Schrock, R. R., Parshall, G. W.: Chem. Rev. 76, 243 (1976)

    Google Scholar 

  60. Baird, M. C.: J. Organomet. Chem. 64, 289 (1974)

    Google Scholar 

  61. Braterman, P. S.: Top. Curr. Chem. 92, 149 (1980)

    Google Scholar 

  62. Akermark, B., Ljungqvist, A. J.: Organomet. Chem. 182, 59 (1979)

    Google Scholar 

  63. Herman, D. F., Nelson, W. K.: J. Am. Chem. Soc. 74, 2693 (1952)

    Google Scholar 

  64. Herman, D. F., Nelson, W. K.: J. Am. Chem. Soc. 75, 3877 (1953)

    Google Scholar 

  65. Herman, D. F., Nelson, W. K.: J. Am. Chem. Soc. 75, 3882 (1953)

    Google Scholar 

  66. Beermann, C., Bestian, H.: Angew. Chem. 71, 618 (1959)

    Google Scholar 

  67. Clauss, K.: Liebigs Ann. Chem. 711, 19 (1968)

    Google Scholar 

  68. Clauss, K., Bestian, H.: Liebigs Ann. Chem. 654, 8 (1962)

    Google Scholar 

  69. Rausch, M. D., Gordon, H. B.: J. Organomet. Chem. 74, 85 (1974)

    Google Scholar 

  70. Kühlein, K., Clauss, K.: Makromol. Chem. 155, 145 (1972)

    Google Scholar 

  71. Sugahara, H., Shuto, Y.: J.Organomet. Chem. 24, 709 (1970)

    Google Scholar 

  72. Yoshino, A., Shuto, Y., Iitaka, Y.: Acta Crystall., Sect. B, 26, 744 (1970)

    Google Scholar 

  73. Reetz, M. T., Westermann, J.: unpublished results 1979–80, Univ. Bonn

    Google Scholar 

  74. Roberts, R. M. G.: J. Organomet. Chem. 63, 159 (1973)

    Google Scholar 

  75. Collier, M. R., Lappert, M. F., Pearce, R.: J. Chem. Soc., Dalton Trans. 1973, 445

    Google Scholar 

  76. Clauss, K., Beermann, C.: Angew. Chem. 71, 627 (1959)

    Google Scholar 

  77. Berthold, H. J., Groh, G.: Z. Anorg. Chem. 319, 230 (1963)

    Google Scholar 

  78. Müller, J., Thiele, K. H.: Z. Anorg. Chem. 362, 120 (1968)

    Google Scholar 

  79. Bürger, H., Neese, H. J.: J. Organomet. Chem. 20, 129 (1969)

    Google Scholar 

  80. Bürger, H., Neese, H. J.: J. Organomet. Chem. 21, 381 (1970)

    Google Scholar 

  81. Neese, H. J., Bürger, H.: J. Organomet. Chem. 32, 213 (1971)

    Article  Google Scholar 

  82. Bürger, H., Neese, H. J.: J. Organomet. Chem. 36, 101 (1972)

    Article  Google Scholar 

  83. Thiele, K. H. et al.: Z. Anorg. Chem. 378, 62 (1970)

    Article  Google Scholar 

  84. Reetz, M. T., Westermann, J., Steinbach, R.: Angew. Chem. 92, 931 (1980); Angew. Chem., Int. Ed. Engl. 19, 900 (1980)

    Google Scholar 

  85. Gray, A. P., Callear, A. B., Edgecombe, F. H. C.: Can. J. Chem. 41, 1502 (1963)

    Google Scholar 

  86. Gorisch, R. D.: J. Am. Chem. Soc. 82, 4211 (1960)

    Article  Google Scholar 

  87. Thiele, K. H.: Pure Appl. Chem. 30, 575 (1972)

    Google Scholar 

  88. Dong, D.: Inorg. Chim. Acta 29, L225 (1978)

    Google Scholar 

  89. Bassi, I. W. et al.: J. Am. Chem. Soc. 93, 3787 (1971)

    Article  Google Scholar 

  90. Davies, G. R., Jarvis, J. A. J., Kilbourn, B. T.: Chem. Comm. 1971, 1511

    Google Scholar 

  91. Davies, G. R. et al.: Chem. Comm. 1971, 677

    Google Scholar 

  92. Evans, D. A., Nelson, J. V., Taber, T. R.: Topics in Stereochem., 13, 1 (1982)

    Google Scholar 

  93. Telnoi, V. I. et al.: Dokl. Akad. Nauk (SSSR) 174, 1374 (1967)

    Google Scholar 

  94. Lappert, M. F., Patil, D. S., Pedley, J. B.: Chem. Comm. 1975, 830

    Google Scholar 

  95. review: Connor, J. A.: Top. Curr. Chem. 71, 71 (1977)

    Google Scholar 

  96. Cox, J. D., Pilcher, G.: Thermochemistry of Organic and Organometallic Compounds, London, Academic Press 1970

    Google Scholar 

  97. Dijkgraaf, C., Rousseau, J. P. G.: Spectrochim. Acta, A, 25, 1455 (1969)

    Article  Google Scholar 

  98. See ref. 1b, p. 19

    Google Scholar 

  99. Armstrong, D. R., Perkins, P. G., Stewart, J. J. P.: Rev. Roumaine Chim. 20, 177 (1975)

    Google Scholar 

  100. Hotokka, M., Pyykkö, P.: J. Organomet. Chem. 174, 289 (1979)

    Article  Google Scholar 

  101. Blustin, P. H.: J. Organomet. Chem. 210, 357 (1981)

    Article  Google Scholar 

  102. Graham, G. D., Marynick, D. S., Lipscomb, W. N.: J. Am. Chem. Soc. 102, 4572 (1980)

    Article  Google Scholar 

  103. Jemmis, E. D., Chandrasekhar, J., Schleyer, P. v. R.: J. Am. Chem. Soc. 101, 2848 (1979)

    Article  Google Scholar 

  104. Streitwieser, A. et al.: J. Am. Chem. Soc. 98, 4778 (1976)

    Article  Google Scholar 

  105. Cassoux, P., Crasnier, F., Laberre, J. F.: J. Organomet. Chem. 165, 303 (1979)

    Article  Google Scholar 

  106. McKinney, R. J.: Chem. Comm. 1980, 490; and lit. cited therein

    Google Scholar 

  107. Lappert, M. F., Pedley, J. B., Sharp, G.: J. Organomet. Chem. 66, 271 (1974)

    Article  Google Scholar 

  108. Basso-Bert, M. et al.: J. Organomet. Chem. 136, 201 (1977)

    Article  Google Scholar 

  109. Caulton, K. G. et al.: J. Am. Chem. Soc. 102, 3009 (1980)

    Article  Google Scholar 

  110. Caulton, K. G. et al.: J. Organomet. Chem. 201, 389 (1980)

    Article  Google Scholar 

  111. Blandy, C., Guerreiro, M. R., Gervais, D.: C. R. Acad. Sc., Serie C, 278, 1323 (1974)

    Google Scholar 

  112. McAlees, A. J., McCrindle, R., Moon-Fat, A. R.: Inorg. Chem. 15, 1065 (1976); and lit. cited therein

    Article  Google Scholar 

  113. Ireland, R.: Organic Synthesis, Englewood Cliffs, N.J., Prentice Hall 1969

    Google Scholar 

  114. Nützel, K.: in Houben-Weyl-Müller, Methoden der Organischen Chemie, Vol. 13/2a, p. 47, Stuttgart, Thieme-Verlag 1973

    Google Scholar 

  115. Schöllkopf, U.: in Houben-Weyl-Müller, Methoden der Organischen Chemie, Vol. 13/1, p. 87, Stuttgart 1970

    Google Scholar 

  116. Kharasch, M. S., Cooper, J. H.: J. Org. Chem. 10, 46 (1945)

    Article  Google Scholar 

  117. Vaskan, R. N. et al.: Zh. Org. Khim. 11, 1818 (1975)

    Google Scholar 

  118. Reetz, M. T., Westermann, J.: unpublished results, Univ. Bonn 1980

    Google Scholar 

  119. Nützel, K.: in Houben-Weyl-Müller, Methoden der Organischen Chemie, Vol. 13/2a, p. 553, Stuttgart, Thieme-Verlag 1973

    Google Scholar 

  120. Nützel, K.: in Houben-Weyl-Müller, Methoden der Organischen Chemie, Vol. 13/2, p. 859, Stuttgart, Thieme-Verlag 1973

    Google Scholar 

  121. Yamamoto, Y. et al.: J. Org. Chem. 47, 119 (1982)

    Article  Google Scholar 

  122. Cahiez, G., Bernard, D., Normant, J. F.: Synthesis 1977, 130

    Google Scholar 

  123. Kauffmann, T., Hamsen, A., Beirich, C.: Angew. Chem. 94; 145 (1982); Angew. Chem., Int. Ed. Engl. 21, 144 (1982).

    Google Scholar 

  124. The early part of our work was reported in lectures presented at Univ. München, (November 10, 1979) and Bayer AG, Krefeld (November 15, 1979)

    Google Scholar 

  125. Reetz, M. T. et al.: Angew. Chem. 92, 1044 (1980); Angew. Chem., Int. Ed. Engl. 19, 1011 (1980)

    Google Scholar 

  126. Peter, R.: Diplomarbeit, Univ. Marburg 1981

    Google Scholar 

  127. Reetz, M. T., Westermann, J., Steinbach, R.: Angew. Chem. 92, 933 (1980); Angew. Chem., Int. Ed. Engl. 19, 901 (1980)

    Google Scholar 

  128. Reetz, M. T.: Schriftenreihe 30 Jahre Fonds der Chemischen Ind., Frankfurt 1980

    Google Scholar 

  129. Weidmann, B., Seebach, D.: Helv. Chim. Acta 63, 2451 (1980)

    Article  Google Scholar 

  130. Reetz, M. T. et al.: unpublished results, Univ. Marburg 1980–82

    Google Scholar 

  131. Weidmann, B. et al.: Helv. Chim. Acta 64, 357 (1981)

    Article  Google Scholar 

  132. Reetz, M. T., Maus, S.: in preparation

    Google Scholar 

  133. Weidmann, B., Maycock, C. D., Seebach, D.: Helv. Chim. Acta 64, 1552 (1981)

    Article  Google Scholar 

  134. TiCl4 and Ti(OR)4 are cheap raw materials used in large quantities in industry. Zirconium analogs cost about 3–4 times as much

    Google Scholar 

  135. Reetz, M. T. et al.: submitted for publication

    Google Scholar 

  136. Reetz, M. T. et al.: Angew. Chem. 94, 133 (1982); Angew. Chem., Int. Ed. Engl. 21, 135 (1982); Angew. Chem. Suppl. 1982, 257–268

    Google Scholar 

  137. See Ref. 13, footnote 65

    Google Scholar 

  138. Kostova, K. et al.: Helv. Chim. Acta 65, 249 (1982)

    Article  Google Scholar 

  139. Schlosser, M.: Struktur und Reaktivität polarer Organometalle, Berlin, Springer-Verlag 1973

    Google Scholar 

  140. Wakefield, B. J.: The Chemistry of Organolithium Compounds, N.Y., Pergamon Press 1974

    Google Scholar 

  141. Pinkus, A. G., Servoss, W. C.: J. Chem. Soc. Perkin II 1979, 1600

    Google Scholar 

  142. Levina, R. Y. et al.: Zh. Obshch. Kim. 32, 1377 (1962)

    Google Scholar 

  143. Berthold, H. J., Groh, G.: Angew. Chem. 78, 495 (1966); Angew. Chem., Int. Ed. Engl. 5, 516 (1966)

    Google Scholar 

  144. Reetz, M. T., Wenderoth, B., Stninbach, R.: submitted for publication

    Google Scholar 

  145. Review: Hoffmann, R. W.: Angew. Chem., 94, 569 (1982)

    Google Scholar 

  146. Okude, Y. et al.: J. Am. Chem. Soc. 99, 3179 (1977)

    Article  Google Scholar 

  147. Naruta, Y., Ushida, S., Maruyama, K.: Chem. Lett. 1979, 919

    Google Scholar 

  148. Cram, D. J., Elhafez, F. A. A.: J. Am. Chem. Soc. 74, 5828 (1952)

    Article  Google Scholar 

  149. Cram. D. J., Allinger, J.: J. Am. Chem. Soc. 76, 4516 (1954)

    Article  Google Scholar 

  150. Cram, D. J., Kopecky, K. R.: J. Am. Chem. Soc. 81, 2748 (1959)

    Article  Google Scholar 

  151. Morrison, J. D., Mosher, H. S.: Asymmetric Organic Reactions, Englewood Cliffs, N. J., Prentice Hall 1971

    Google Scholar 

  152. Anh, N. T.: Top. Curr. Chem. 88, 40 (1980)

    Google Scholar 

  153. Jones, P. R., Goller, E. J., Kauffman, W. J.: J. Org. Chem. 36, 3311 (1971)

    Article  Google Scholar 

  154. Kauffmann, W. J.: J. Org. Chem. 36, 3311 (1971)

    Article  Google Scholar 

  155. Clark, R. J. H., McAlees, A. J.: Inorg. Chem. 11, 342 (1972)

    Article  Google Scholar 

  156. Reetz, M. T., Westermann, J.: Synth. Comm. 11, 647 (1981)

    Google Scholar 

  157. Makino, T.: J. Org. Chem. 43, 276 (1978)

    Article  Google Scholar 

  158. Piatak, D. M., Wicha, J.: Chem. Rev. 78, 199 (3978)

    Article  Google Scholar 

  159. Stocker, J. H. at al.: J. Am. Chem. Soc. 82, 3913 (1960)

    Article  Google Scholar 

  160. Marsella, J. A., Moloy, K. G., Caulton, K. G.: J. Organomet. Chem. 201, 389 (1980)

    Article  Google Scholar 

  161. Reetz, M. T., Steinbach, R.: unpublished results, Univ. Marburg 1982

    Google Scholar 

  162. Wolfrom, M. L., Hanessian, S.: J. Org. Chem. 27, 1800 (1962)

    Google Scholar 

  163. Inch. T. D.: Carbohydrate Res. 5, 45 (1967)

    Article  Google Scholar 

  164. Still, W. C., Schneider, J. A.: Tetrahedron Lett. 1980 1035

    Google Scholar 

  165. Narasaka, K.: Chem. Lett. 1980, 1415

    Google Scholar 

  166. Ashby, E. C., Laemmle, J. T.: Chem. Rev. 75, 521 (1975)

    Article  Google Scholar 

  167. Ashby, E. C., Noding, S. A.: J. Org. Chem. 44, 4371 (1979)

    Article  Google Scholar 

  168. MacDonald, T. L., Still, W. C.: J. Am. Chem. Soc. 97, 5280 (1975)

    Article  Google Scholar 

  169. Heathcock, C. H.: Comprehensive Carbanion Chemistry, Vol. II, ((ed.) Durst, T., Buncel, E.), Amsterdam, Elsevier 1981

    Google Scholar 

  170. Evans, D. A., McGee, L. R.: Tetrahedron Lett. 1980, 3975

    Google Scholar 

  171. Yamamoto, Y., Maruyama, K.: Tetrahedron Lett. 1980, 4607

    Google Scholar 

  172. Yamamoto, Y., Yatagai, H., Maruyama, K.: Chem. Comm. 1981, 162

    Google Scholar 

  173. Noyori, R., Nishida, I., Sakata, J.: J. Am. Chem. Soc. 103, 2106 (1981)

    Google Scholar 

  174. Evans, D. A., McGee, L. R.: J. Am. Chem. Soc. 103, 2876 (1981)

    Article  Google Scholar 

  175. Stork, G., Shiner, C. S., Winkler, J. D.: J. Am. Chem. Soc. 104, 310 (1982)

    Article  Google Scholar 

  176. Posner, G. H.: Pure Appl. Chem. 53, 2307 (1981)

    Google Scholar 

  177. Reetz, M. T., Steinbach, R., Keßeler, K.: Angew. Chem., in press

    Google Scholar 

  178. Corey, E. J., Enders, D.: Chem. Ber. 111, 1337 (1978)

    Google Scholar 

  179. Davenport, K. G. et al.: J. Am. Chem. Soc. 101, 5654 (1979)

    Article  Google Scholar 

  180. Hoffmann, R. W. et al.: J. Org. Chem. 46, 1309 (1981)

    Article  Google Scholar 

  181. Yamamoto, Y. et al.: J. Am. Chem. Soc. 102, 7107 (1980)

    Article  Google Scholar 

  182. Sato, F., Iijima, S., Sato, M.: Tetrahedron Lett. 1981, 243

    Google Scholar 

  183. Sato, F. et al.: Chem. comm. 1981, 1140

    Google Scholar 

  184. Yamamoto, Y., Maruyama, K.: Tetrahedron Lett. 1981, 2895

    Google Scholar 

  185. Tsai, D. J. S., Matteson, D. S.: Tetrahedron Lett. 1981, 2751

    Google Scholar 

  186. Hanko, R., Hoppe, D.: Angew. Chem., 94, 378 (1982); Angew. Chem., Int. Ed. Engl. 21, 372 (1982)

    Google Scholar 

  187. Olivero, A. G., Weidmann, B., Seebach, D.: Helv. Chim. Acta 64, 2485 (1981)

    Article  Google Scholar 

  188. Trost, B. M.: Acc. Chem. Res. 7, 85 (1974)

    Article  Google Scholar 

  189. Noller, C. R.: J. Am. Chem. Soc. 51, 594 (1929)

    Article  Google Scholar 

  190. Buck, R. F.: J. Inst. Petrol. 34, 339 (1948)

    Google Scholar 

  191. Kennedy, J. P., Desai, U. V., Sivaram, S.: J. Am. Chem. Soc. 95, 6386 (1973)

    Article  Google Scholar 

  192. see however: Beckhaus, H. D., Hellmann, G., Rüchardt, C.: Chem. Ber. 111, 72 (1978)

    Google Scholar 

  193. Reetz, M. T. et al.: Chem. Comm. 1980, 1202

    Google Scholar 

  194. Reetz, M. T., Stephan, W.: J. Chem. Res. 1981, (S) 44; J. Chem. Res. 1981, (M) 0583-0594

    Google Scholar 

  195. Reetz, M. T., Westermann, J., Steinbach, R.: Chem. Comm. 1981, 237

    Google Scholar 

  196. Meisters, A., Mole, T.: Aust. J. Chem. 27, 1665 (1974)

    Google Scholar 

  197. Oppolzer, W., Godel, T.: J. Am. Chem. Soc. 100, 2583 (1978)

    Article  Google Scholar 

  198. Gröger, C., Musso, H., Rossnagel, I.: Chem. Ber. 113, 3621 (1980)

    Google Scholar 

  199. Martin, S. F.: Tetrahedron 36, 419 (1980)

    Article  Google Scholar 

  200. Trost, B. M., Hiemstra, H.: J. Am. Chem. Soc. 104, 886 (1982)

    Article  Google Scholar 

  201. Pataki, J., Konieczny, M., Harvey, R. G.: J. Org. Chem. 47, 1133 (1982)

    Article  Google Scholar 

  202. Reetz, M. T., Westermann, J.: submitted

    Google Scholar 

  203. Review of cannabinoids

    Google Scholar 

  204. Mechoulam, R., McCallum, N. K., Burstein, S.: Chem. Rev. 76, 75 (1976)

    Article  Google Scholar 

  205. Mechoulam, R., Carlini, E. A.: Naturwiss. 65, 174 (1978)

    Article  PubMed  Google Scholar 

  206. Petrzilka, T., Haefliger, W., Sikemeier, C.: Helv. Chim. Acta 52, 1102 (1969)

    Article  Google Scholar 

  207. Singh, V., Kaul, V. V., Martin, A. R.: Synth. Comm. 1981, 429

    Google Scholar 

  208. Reetz, M. T., Steinbach, R., Wenderoth, B.: Synth. Comm. 1981, 261

    Google Scholar 

  209. Posner, G. H., Brunelle, D. J.: Tetrahedron Lett. 1972, 293

    Google Scholar 

  210. Tebbe, F. N., Parshall, G. W., Reddy, G. S.: J. Am. Chem. Soc. 100, 3611 (1978)

    Article  Google Scholar 

  211. Pine, S. H. et al.: J. Am. Chem. Soc. 102, 3270 (1980)

    Article  Google Scholar 

  212. Takai, K. et al.: Tetrahedron Lett. 1978, 2417

    Google Scholar 

  213. Takai, K. et al.: Bull. Chem. Soc. Jap. 53, 1698 (1980)

    Google Scholar 

  214. Kauffmann, T. et al.: Tetrahedron Lett. 1981, 5031

    Google Scholar 

  215. Reetz, M. T., Wenderoth, B.: unpublished results

    Google Scholar 

  216. Widler, L., Seebach, D.: Helv. Chim. Acta 65, 1085 (1982)

    Article  Google Scholar 

  217. Reetz, M. T., Schmidtberger, S.: in preparation

    Google Scholar 

  218. Reetz, M. T., Peter, R.: unpublished results

    Google Scholar 

  219. Reetz, M. T., Westermann, J.: in preparation

    Google Scholar 

  220. Leblanc, J. C., Moise, C., Tirouflet, J.: Nouv. Chim. 1, 211 (1977)

    Google Scholar 

  221. For an excellent review concerning chiral tetrahedral organotransition metal compounds, see Brunner, H.: Adv. Organomet. Chem. 18, 151 (1980)

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

Copyright information

© 1982 Springer-Verlag

About this paper

Cite this paper

Reetz, M.T. (1982). Organotitanium reagents in organic synthesis a simple means to adjust reactivity and selectivity of carbanions. In: Synthetic and Structural Problems. Topics in Current Chemistry, vol 106. Springer, Berlin, Heidelberg. https://doi.org/10.1007/3-540-11766-0_1

Download citation

  • DOI: https://doi.org/10.1007/3-540-11766-0_1

  • Published:

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-540-11766-7

  • Online ISBN: 978-3-540-39481-5

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics