Skip to main content
SpringerLink
Log in

Asymmetrische Katalysen, 39. Mitt.: Monohydrosilane in der enantioselektiven katalytischen Hydrosilylierung prochiraler Ketone

Asymmetric catalyses, XXXIX: Monohydrosilanes in the enantioselective catalytical hydrosilylation of prochiral ketones

  • Anorganische Und Physikalische Chemie
  • Published:
Monatshefte für Chemie / Chemical Monthly Aims and scope Submit manuscript

Abstract

The reactivity of several monohydrosilane/complex systems in the hydrosilylation of acetophenone and benzylmethylketone was investigated. The active systems were modified by addition of optically active ligands and used as enantioselectivein-situ catalysts for the hydrosilylation of the above prochiral ketones which on hydrolysis gave α-phenylethanol and α-benzylethanol in up to 18% ee.

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. 38. Mitt.:Brunner H, Kürzinger A, Wiegrebe W (1987) Arch Pharm (Weinheim) 321: 73

    Google Scholar 

  2. Yamamoto K,Hayashi T,Kumada M (1972) J Organomet Chem 46: C 65

  3. Ojima I, Hirai K (1985) Asymmetric synthesis, vol 5. Academic Press, New York, p 103

    Google Scholar 

  4. Bosnich B (1986) Asymmetric catalysis. Martinus Nijhoff, Dordrecht, p 35

    Google Scholar 

  5. Johnson TH, Klein C, Thomen S (1981) J Mol Catal 12: 3

    Google Scholar 

  6. Brunner H, Reiter B, Riepl G (1984) Chem Ber 117: 1330

    Google Scholar 

  7. Brunner H, Becker R, Riepl G (1984) Organometallics 3: 1354

    Google Scholar 

  8. Produkte der Wacker-Chemie AG (Burghausen)

  9. Pearce CA (1972) Silicon chemistry and applications. The Chemical Society London, London

    Google Scholar 

  10. Ullmanns Enzyklopädie der Technischen Chemie (1982) 4. Aufl, Bd 21. Verlag Chemie, Weinheim, p 485

  11. Fisch H (1984) Diplomarbeit, Universität Regensburg

  12. Yamamoto K,Hayashi T,Kumada M (1971) J Organomet Chem 28: C 37

  13. Yamamoto K, Hayashi T, Kumada M (1971) J Am Chem Soc 93: 5301

    Google Scholar 

  14. Yamamoto K, Hayashi T, Kumada M (1976) J Organomet Chem 112: 253

    Google Scholar 

  15. Tsipis LA (1980) J Organomet Chem 187: 427

    Google Scholar 

  16. Cornish AJ, Lappert MF, Filatova GL, Nile TA (1979) J Organomet Chem 153: 172

    Google Scholar 

  17. Wang LZ, Yiang YY (1983) J Organomet Chem 251: 39

    Google Scholar 

  18. Lappert MF, Nile TA (1975) J Organomet Chem 102: 543

    Google Scholar 

  19. Matsumoto M, Hashima Y, Nagai Y (1981) Bull Chem Soc Jpn 54: 1279

    Google Scholar 

  20. Saam JC, Speier JL (1958) J Am Chem Soc 80: 4104

    Google Scholar 

  21. Satsuk EI (1976) Izv Akad Nauk SSSR Ser Khim 6: 1318

    Google Scholar 

  22. Nogaideli AI, Chogovadze TV, Nogaideli GA (1976) Sobshch Akad Nauk Gruz SSSR 82: 1318

    Google Scholar 

  23. Andrianov KA, Zavin BG, Erdokimow AM, Budanova OV (1974) Zh Obshch Khim 44: 2140

    Google Scholar 

  24. Yoshi E, Ikeshima H, Ozaki K (1972) Chem Pharm Bull 20: 1827

    Google Scholar 

  25. Tarverdiev S, Sultanov RA, Baranov GK, Khudarayov IA (1974) Zh Obshch Khim 44: 1511

    Google Scholar 

  26. Rumin B (1983) J Organomet Chem 247: 351

    Google Scholar 

  27. Bartsch R (1982) Pharmazie 137: 483

    Google Scholar 

  28. Michalska ZM, Capka M, Stoch J (1981) J Mol Catal 11: 323

    Google Scholar 

  29. Hayashi T, Yamamoto K, Omizu H, Kumada M (1976) J Organomet Chem 113: 127

    Google Scholar 

  30. Mushegyan NG, Vartanyan AG, Melikyan MO (1979) Arm Khim Zv 32: 120.

    Google Scholar 

  31. Semmelhack M, Misra RN (1982) J Org Chem 47: 2469

    Google Scholar 

  32. Göndös G,Orr JC (1982) J Chem Soc Chem Comm: 1238

  33. Lipowitz J, Bowman J (1973) J Org Chem 38: 162

    Google Scholar 

  34. Langlois N,Dang TP,Kagan HB (1973) Tetrahedron Lett: 4865

  35. Dumont W, Poulin JC, Dang TP, Kagan HB (1973) J Am Chem Soc 95: 8295

    Google Scholar 

  36. Brunner H, Riepl G, Weitzer H (1983) Angew Chem 95: 326; Angew Chem Int Ed Engl 22: 331; Suppl 445

    Google Scholar 

  37. Brunner H, Schmidt M, Unger G, Schönenberger H (1985) Eur J Med Chem 20: 509

    Google Scholar 

  38. Brunner H, Doppelberger J (1978) Chem Ber 111: 673

    Google Scholar 

  39. Brunner H, Pieronczyk W (1979) Angew Chem 91: 655; Angew Chem Int Ed Engl 18: 620

    Google Scholar 

  40. Kagan HB, Dang TP (1972) J Am Chem Soc 94: 6429

    Google Scholar 

  41. Horner L, Skaletz DM (1975) Liebigs Ann Chem 6: 1210

    Google Scholar 

Download references

Author information

Authors and Affiliations

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

    Henri Brunner & Heinrich Fisch

Authors
  1. Henri Brunner
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Heinrich Fisch
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Brunner, H., Fisch, H. Asymmetrische Katalysen, 39. Mitt.: Monohydrosilane in der enantioselektiven katalytischen Hydrosilylierung prochiraler Ketone. Monatsh Chem 119, 525–532 (1988). https://doi.org/10.1007/BF00809204

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00809204

Keywords

Search

Navigation