Monatshefte für Chemie / Chemical Monthly

, Volume 119, Issue 5, pp 525–532 | Cite as

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

  • Henri Brunner
  • Heinrich Fisch
Anorganische Und Physikalische Chemie

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

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.

Keywords

Monohydrosilanes Enantioselective hydrosilylation Prochiral ketones 

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Literatur

  1. [1]
    38. Mitt.:Brunner H, Kürzinger A, Wiegrebe W (1987) Arch Pharm (Weinheim) 321: 73Google Scholar
  2. [2]
    Yamamoto K,Hayashi T,Kumada M (1972) J Organomet Chem 46: C 65Google Scholar
  3. [3]
    Ojima I, Hirai K (1985) Asymmetric synthesis, vol 5. Academic Press, New York, p 103Google Scholar
  4. [4]
    Bosnich B (1986) Asymmetric catalysis. Martinus Nijhoff, Dordrecht, p 35Google Scholar
  5. [5]
    Johnson TH, Klein C, Thomen S (1981) J Mol Catal 12: 3Google Scholar
  6. [6]
    Brunner H, Reiter B, Riepl G (1984) Chem Ber 117: 1330Google Scholar
  7. [7]
    Brunner H, Becker R, Riepl G (1984) Organometallics 3: 1354Google Scholar
  8. [8]
    Produkte der Wacker-Chemie AG (Burghausen)Google Scholar
  9. [9]
    Pearce CA (1972) Silicon chemistry and applications. The Chemical Society London, LondonGoogle Scholar
  10. [10]
    Ullmanns Enzyklopädie der Technischen Chemie (1982) 4. Aufl, Bd 21. Verlag Chemie, Weinheim, p 485Google Scholar
  11. [11]
    Fisch H (1984) Diplomarbeit, Universität RegensburgGoogle Scholar
  12. [12]
    Yamamoto K,Hayashi T,Kumada M (1971) J Organomet Chem 28: C 37Google Scholar
  13. [13]
    Yamamoto K, Hayashi T, Kumada M (1971) J Am Chem Soc 93: 5301Google Scholar
  14. [14]
    Yamamoto K, Hayashi T, Kumada M (1976) J Organomet Chem 112: 253Google Scholar
  15. [15]
    Tsipis LA (1980) J Organomet Chem 187: 427Google Scholar
  16. [16]
    Cornish AJ, Lappert MF, Filatova GL, Nile TA (1979) J Organomet Chem 153: 172Google Scholar
  17. [17]
    Wang LZ, Yiang YY (1983) J Organomet Chem 251: 39Google Scholar
  18. [18]
    Lappert MF, Nile TA (1975) J Organomet Chem 102: 543Google Scholar
  19. [19]
    Matsumoto M, Hashima Y, Nagai Y (1981) Bull Chem Soc Jpn 54: 1279Google Scholar
  20. [20]
    Saam JC, Speier JL (1958) J Am Chem Soc 80: 4104Google Scholar
  21. [21]
    Satsuk EI (1976) Izv Akad Nauk SSSR Ser Khim 6: 1318Google Scholar
  22. [22]
    Nogaideli AI, Chogovadze TV, Nogaideli GA (1976) Sobshch Akad Nauk Gruz SSSR 82: 1318Google Scholar
  23. [23]
    Andrianov KA, Zavin BG, Erdokimow AM, Budanova OV (1974) Zh Obshch Khim 44: 2140Google Scholar
  24. [24]
    Yoshi E, Ikeshima H, Ozaki K (1972) Chem Pharm Bull 20: 1827Google Scholar
  25. [25]
    Tarverdiev S, Sultanov RA, Baranov GK, Khudarayov IA (1974) Zh Obshch Khim 44: 1511Google Scholar
  26. [26]
    Rumin B (1983) J Organomet Chem 247: 351Google Scholar
  27. [27]
    Bartsch R (1982) Pharmazie 137: 483Google Scholar
  28. [28]
    Michalska ZM, Capka M, Stoch J (1981) J Mol Catal 11: 323Google Scholar
  29. [29]
    Hayashi T, Yamamoto K, Omizu H, Kumada M (1976) J Organomet Chem 113: 127Google Scholar
  30. [30]
    Mushegyan NG, Vartanyan AG, Melikyan MO (1979) Arm Khim Zv 32: 120.Google Scholar
  31. [31]
    Semmelhack M, Misra RN (1982) J Org Chem 47: 2469Google Scholar
  32. [32]
    Göndös G,Orr JC (1982) J Chem Soc Chem Comm: 1238Google Scholar
  33. [33]
    Lipowitz J, Bowman J (1973) J Org Chem 38: 162Google Scholar
  34. [34]
    Langlois N,Dang TP,Kagan HB (1973) Tetrahedron Lett: 4865Google Scholar
  35. [35]
    Dumont W, Poulin JC, Dang TP, Kagan HB (1973) J Am Chem Soc 95: 8295Google Scholar
  36. [36]
    Brunner H, Riepl G, Weitzer H (1983) Angew Chem 95: 326; Angew Chem Int Ed Engl 22: 331; Suppl 445Google Scholar
  37. [37]
    Brunner H, Schmidt M, Unger G, Schönenberger H (1985) Eur J Med Chem 20: 509Google Scholar
  38. [38]
    Brunner H, Doppelberger J (1978) Chem Ber 111: 673Google Scholar
  39. [39]
    Brunner H, Pieronczyk W (1979) Angew Chem 91: 655; Angew Chem Int Ed Engl 18: 620Google Scholar
  40. [40]
    Kagan HB, Dang TP (1972) J Am Chem Soc 94: 6429Google Scholar
  41. [41]
    Horner L, Skaletz DM (1975) Liebigs Ann Chem 6: 1210Google Scholar

Copyright information

© Springer-Verlag 1988

Authors and Affiliations

  • Henri Brunner
    • 1
  • Heinrich Fisch
    • 1
  1. 1.Institut für Anorganische ChemieUniversität RegensburgRegensburgBundesrepublik Deutschland

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