Skip to main content
SpringerLink
Log in

Hydrierung prochiraler Olefine mit Rhodium-Komplexen von optisch aktiven Amidinen

Hydrogenation of prochiral olefins with rhodium complexes of optically active amidines

Asymmetrische Katalysen, 4. Mitt.

  • Organic Chemistry and Biochemistry
  • Published:
Monatshefte für Chemie / Chemical Monthly Aims and scope Submit manuscript

Abstract

[RhCl(C8H14)2]2 together with the optically active amidines C6H5C(=NR)NHCH(CH3) (C6H5) I–V or their Li derivatives after activation with molecular hydrogen gives catalysts which at room temperature and 1.1 bar H2-pressure hydrogenate the prochiral substrates (Z)-α[N-acetylamino]-cinnamic acid, itaconic acid, α-methylcinnamic acid, α-methylcinnamic aldehyde, and α-methylcinnamic alcohol as well as cyclohexene, benzene and toluene. Good hydrogenation activity of the new catalysts is in contrast to low optical induction which only in the hydrogenation of α-methylcinnamic alcohol with 1.5 to 2% leads to values different from zero.

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

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

Literatur

  1. H. B. Kagan, Pure Appl. Chem.43, 401 (1975).

    Google Scholar 

  2. J. D. Morrison, W. F. Masler undS. Hathaway, Catal. Org. Syn.1976, 203.

  3. J. D. Morrison, W. F. Masler undK. M. Neuberg, Adv. Catal.25, 81 (1976).

    Google Scholar 

  4. R. Pearce, Catalysis2, 176 (1978).

    Google Scholar 

  5. D. Valentine undJ. W. Scott, Synthesis5, 329 (1978).

    Google Scholar 

  6. C. White, Organomet. Chem.7, 367 (1978).

    Google Scholar 

  7. J. Halpern, Trans. Amer. Crystallogr. Assoc.14, 59 (1978).

    Google Scholar 

  8. J. Halpern, T. Okamoto undA. Zakhariev, J. Molec. Catalysis2, 65 (1976).

    Google Scholar 

  9. R. H. Crabtree, H. Felkin, T. Fillebeen-Khan undG. E. Morris, J. Organometal. Chem.168, 183 (1979).

    Google Scholar 

  10. I. Bernal, S. J. LaPlaca, J. Korp, H. Brunner undW. A. Herrmann, Inorg. Chem.17, 382 (1978).

    Google Scholar 

  11. H. Brunner, Acc. Chem. Res.12, 250 (1979).

    Google Scholar 

  12. H. Brunner, Top. Curr. Chem.56, 65 (1975).

    Google Scholar 

  13. H. Brunner, Adv. Organometal. Chem., im Druck.

  14. P. Hofmann, Angew. Chem.89, 551 (1977); Angew. Chem. Int. Ed. Engl.16, 536 (1977).

    Google Scholar 

  15. P. B. Hitchcock, M. McPartlin undR. Mason, Chem. Commun.1969, 1367.

  16. H. Brunner, W. A. Herrmann undJ. Wachter, J. Organometal. Chem.107, C 11 (1976).

    Google Scholar 

  17. H. Brunner undJ. Wachter, Chem. Ber.110, 721 (1977).

    Google Scholar 

  18. M. G. Reisner, I. Bernal, H. Brunner undJ. Wachter, J. Organometal. Chem.137, 329 (1977).

    Google Scholar 

  19. H. Brunner undR. Lukas, Chem. Ber.112, 2528 (1979).

    Google Scholar 

  20. H. Brunner, I. Bauer undR. Lukas, Z. Naturforsch., im Druck.

  21. H. Brunner undD. K. Rastogi, Inorg. Chem., im Druck.

  22. H. Brunner, G. Agrifoglio undJ. Lukassek, J. Organometal. Chem., im Druck.

  23. J. Chatt undL. M. Venzani, J. Chem. Soc.1957, 4735.

  24. R. Cramer, Inorg. Chem.1, 722 (1963).

    Google Scholar 

  25. L. Perri, A. Lionetti, G. Allegra undA. Immirzi, Chem. Commun.1965, 336.

  26. R. R. Schrock undJ. A. Osborn, J. Amer. Chem. Soc.98, 2134 (1976).

    Google Scholar 

  27. R. Uson, L. A. Oro, M. A. Garralda, M. C. Claver undP. Lahuerta, Trans. Met. Chem.4, 55 (1979).

    Google Scholar 

  28. R. L. Shriner undF. W. Neumann, Chem. Rev.35, 351 (1944).

    Google Scholar 

  29. S. Patai, The Chemistry of Amidines and Imidates. New York: Wiley. 1975.

    Google Scholar 

  30. M. Freifelder, Practical Catalytic Hydrogenation. New York: Wiley. 1971.

    Google Scholar 

  31. M. Freifelder, Catalytic Hydrogenation in Organic Synthesis, Procedures and Commentary. New York: Wiley. 1978.

    Google Scholar 

  32. W. Bradley undI. Wight, J. Chem. Soc.1956, 640.

  33. T. Inglis, M. Kilner, T. Reynoldson undE. E. Robertson, J. Chem. Soc. Dalton1975, 924.

  34. T. Inglis undM. Kilner, J. Chem. Soc. Dalton1975, 930.

  35. L. Tonioli, A. Immirzi, U. Croatto undG. Bombiere, Inorg. Chim. Acta19, 209 (1976).

    Google Scholar 

  36. P. Hendriks, J. Kuyper undK. Vrieze, J. Organometal. Chem.120, 285 (1976).

    Google Scholar 

  37. S. D. Robinson undA. Sahajpal, J. Organometal. Chem.117, C 111 (1976).

    Google Scholar 

  38. L. D. Brown, S. D. Robinson, A. Sahajpal undJ. A. Ibers, Inorg. Chem.16, 2728 (1977).

    Google Scholar 

  39. W. H. De Roode, K. Vrieze, E. A. Koerner von Gustorf undA. Ritter, J. Organometal. Chem.135, 183 (1977).

    Google Scholar 

  40. N. G. Connelly, H. Daykin undZ. Demidowicz, J. Chem. Soc. Dalton1978, 1532.

  41. H. Brunner undJ. Wachter, J. Chem. Res. (S)1978, 136; (M)1978, 1801.

  42. W. H. De Roode, M. L. Beekes, A. Oskam undK. Vrieze, J. Organometal. Chem.142, 337 (1977).

    Google Scholar 

  43. W. H. De Roode undK. Vrieze, J. Organometal. Chem.145, 207 (1978).

    Google Scholar 

  44. W. H. De Roode undK. Vrieze J. Organometal. Chem.153, 345 (1978).

    Google Scholar 

  45. W. H. De Roode, J. Berke, A. Oskam undK. Vrieze, J. Organometal. Chem.155, 307 (1978).

    Google Scholar 

  46. W. H. De Roode, D. G. Prins, A. Oskam undK. Vrieze, J. Organometal. Chem.154, 273 (1978).

    Google Scholar 

  47. A. D. Harris, S. D. Robinson undA. Sahajpal, J. Organometal. Chem.174, C 11 (1979).

    Google Scholar 

  48. P. Abley undF. J. McQuillin, J. Chem. Soc. C1971, 844.

  49. R. Glaser, M. Twaik, S. Geresh undJ. Blumenfeld, Tetrahedron Lett.1977, 4635.

  50. E. J. Eisenbraun undM. S. McElvain, J. Amer. Chem. Soc.77, 3383 (1955).

    Google Scholar 

  51. A. W. Schrecker, J. Org. Chem.22, 33 (1957).

    Google Scholar 

  52. D. Enders undH. Eichenau, Tetrahedron Lett.1977, 191.

  53. S. Terashima, M. Nara undS. Yamada, Chem. Pharm. Bull.18, 1124 (1970).

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institut für Chemie, Universität Regensburg, D-8400, Regensburg, Bundesrepublik Deutschland

    Henri Brunner & Giuseppe Agrifoglio

Authors
  1. Henri Brunner
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Giuseppe Agrifoglio
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

3. Mitt.:H. Brunner undW. Pieronczyk, J. Chem. Res., im Druck.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Brunner, H., Agrifoglio, G. Hydrierung prochiraler Olefine mit Rhodium-Komplexen von optisch aktiven Amidinen. Monatshefte für Chemie 111, 275–287 (1980). https://doi.org/10.1007/BF00938734

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00938734

Keywords

Search

Navigation