Skip to main content

Asymmetric Homogeneous Hydrogenation of Prochiral Olefins and Control of the Metal Configuration in Labile Optically Active Organotransition Metal Complexes

  • Conference paper
Catalysis in Chemistry and Biochemistry Theory and Experiment

Part of the book series: The Jerusalem Symposia on Quantum Chemistry and Biochemistry ((JSQC,volume 12))

Abstract

Since 1966 the Wilkinson catalyst RhCl[P(C6H5)3]3 is used for the homogeneous hydrogenation of olefins mostly under conditions as mild as room temperature and hydrogen of atmospheric pressure (1). In 1968 the groups of Horner and Knowles used optically active phosphines instead of triphenylphosphine for the hydrogenation of prochiral olefins and

Scheme 2

Scheme 2

observed the formation of optically active hydrogenation products (2,3). In the past decade progress in the field of catalytic asymmetric hydrogenation of prochiral olefins was mainly associated with the development of new optically active chelate ligands, four examples of which are shown in scheme 1 (4–7).

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

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 129.00
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 169.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 169.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

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. Osborn, J.A., Jardine, F.H., Young, J.F., and Wilkinson, G.: 1966, J. Chem. Soc. A, pp. 1711.

    Google Scholar 

  2. Horner, L., Siegel, H., and Büthe, H.: 1968, Angew.Chem. 80, pp. 1034;

    Article  Google Scholar 

  3. Knowles, W.S. and Sabacky, M.J.: 1968, JCS Chem.Comm., pp. 1445.

    Google Scholar 

  4. Kagan, H.B. and Dang, T.P.: 1972, J.Amer.Chem.Soc. 94, pp. 6429.

    Article  CAS  Google Scholar 

  5. Knowles, W.S., Sabacky, M.J., Vineyard, B.D., and Weinkauf, D.J.: 1975, J.Amer.Chem.Soc. 97, pp. 2567.

    Article  CAS  Google Scholar 

  6. Fryzuk, M.D. and Bosnich, B.: 1977, J.Amer.Chem.Soc. 99, pp. 62 62.

    Google Scholar 

  7. Fryzuk, M.D. and Bosnich, B.: 1978, J.Amer.Chem.Soc. 100, pp. 5491.

    Article  CAS  Google Scholar 

  8. Nesterova, N.P., Medved, T.Y., Polikarpov, Y.M., and Kabachnik, M.K.: 1974, Izv.Akad.Nauk SSSR Ser.Khim. 10, pp. 2210.

    Google Scholar 

  9. Naumann, K., Zon, G., and Mislow, K.: 1969, J. Amer. Chem. Soc. 91, pp. 7013.

    Google Scholar 

  10. Brunner, H. and Pieronczyk, W.: Angew.Chem., in press.

    Google Scholar 

  11. Brunner, H.: 1971, Angew.Chem. 83, pp. 274;

    Article  Google Scholar 

  12. Brunner, H.: 1971, Angew. Chem. int. Ed. Engl. 10, pp. 249.

    Article  CAS  Google Scholar 

  13. Brunner, H.: 1974, Ann. N.Y. Acad. Sci. 239, pp. 213.

    Article  CAS  Google Scholar 

  14. Brunner, H.: 1975, Top. Curr. Chem. 56, pp. 67.

    Article  CAS  Google Scholar 

  15. Brunner, H.: 1977, Chemie in unserer Zeit 11, pp. 157.

    Article  CAS  Google Scholar 

  16. Brunner, H.: Acc. Chem. Res., in press.

    Google Scholar 

  17. Brunner, H.: Adv. Organometal. Chem., in press.

    Google Scholar 

  18. Brunner, H., in Koerner von Gustorf, E.A., Grevels, F.-W., and Fischler, I.: 1978, Organic Chemistry of Iron, Vol. 1, Academic Press, pp. 299.

    Google Scholar 

  19. Brunner, H., Herrmann, W.A., and Wachter, J.: 1976, J.Organometal.Chem. 107, pp. C11.

    Article  CAS  Google Scholar 

  20. Brunner, H. and Wachter, J.: 1977, Chem. Ber. 110, pp. 721.

    Article  CAS  Google Scholar 

  21. Brunner, H. and Lukas, R.: Chem. Ber., in press.

    Google Scholar 

  22. Brunner, H. and Rastogi, D.K.: Inorg. Chem., in press.

    Google Scholar 

  23. Brunner, H., Doppelberger, J., Dreischl, P., and Mol1enberg, T.: 1977, J.Organometal.Chem. 139, p. 223.

    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

© 1979 D. Reidel Publishing Company

About this paper

Cite this paper

Brunner, H. (1979). Asymmetric Homogeneous Hydrogenation of Prochiral Olefins and Control of the Metal Configuration in Labile Optically Active Organotransition Metal Complexes. In: Pullman, B. (eds) Catalysis in Chemistry and Biochemistry Theory and Experiment. The Jerusalem Symposia on Quantum Chemistry and Biochemistry, vol 12. Springer, Dordrecht. https://doi.org/10.1007/978-94-009-9513-0_20

Download citation

  • DOI: https://doi.org/10.1007/978-94-009-9513-0_20

  • Publisher Name: Springer, Dordrecht

  • Print ISBN: 978-94-009-9515-4

  • Online ISBN: 978-94-009-9513-0

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics