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DOI: 10.1039/A902441G (Paper) Reference Section for: Chem. Commun., 1999, 1167-1168

Superior performance of a chiral catalyst confined within mesoporous silica

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Brian F. G. Johnson, Stuart A. Raynor, Douglas S. Shephard, Thomas Mashmeyer, Thomas Mashmeyer, John Meurig Thomas, Gopinthar Sankar, Stefen Bromley, Richard Oldroyd, Lynn Gladden and Mike D. Mantle

Abstract

A chiral catalyst from the ligand 1,1′-bis(diphenylphosphino)ferrocene (dppf) anchored to the inner walls of the mesoporous support MCM-41 and co-ordinated to PdII has been shown to exhibit a degree of regioselectivity and enantiomeric excess, in the allylic amination of cinnamyl acetate, which is far superior to that of its homogeneous counterpart or that of a surface-bound analogue attached to a non-porous silica.

References

  1. R. Noyori, Asymmetric Catalysis in Organic Synthesis, Wiley, New York, 1994 Search PubMed.
  2. J. M. Brown and S. G. Davies, Nature, 1994, 370, 418 CrossRef.
  3. Advances in Catalytic Processes: Asymmetric Chemical Transformations, ed. M. Boyle, JAI, Greenwich, CT, vol. 1. Search PubMed.
  4. A. Pfalz and T. Heinz, Top. Catal., 1997, 4, 229 CrossRef.
  5. A. Baiker, Curr. Opin. Solid State Mater. Sci., 1998, 3, 86 CrossRef CAS.
  6. Top Catal., ed. D. G. Blackmond and W. Leitner, 1997, 4, Part 1. Search PubMed.
  7. A. Corma, M. Iglesias, C. del Pino and F. Sanchez, J. Chem. Soc., Chem. Commun., 1991, 1253 RSC.
  8. J. M. Thomas, Philos. Trans. R. Soc. London, Ser. A, 1990, 333, 173 Search PubMed.
  9. C. L. Hill, Activation and Functionalisation of Alkanes, Wiley, New York, 1989 Search PubMed.
  10. M. J. Sabater, A. Corma, A. Domenech, V. Fornes and H. Garcia, Chem. Commun., 1997, 1285 RSC.
  11. J. M. Thomas, T. Maschmeyer, B. F. G. Johnson and D. S. Shephard, J. Mol. Catal., 1999, 141, 139 Search PubMed.
  12. D. S. Shephard, W. Z. Zhou, T. Mashmeyer, J. M. Matters, C. L. Roper, S. Parsons, B. F. G. Johnson and M. J. Duer, Angew. Chem., Int. Ed., 1998, 37, 2719 CrossRef CAS.
  13. G. W. Gokel and I. K. Ugi, J. Chem. Educ., 1972, 49, 294 CAS.
  14. T. Hayashi, T. Mise, M. Fukushima, M. Kagotani, N. Nagashima, Y. Hamada, A. Matsumoto, S. Kawakami, M. Konishi, K. Yamamoto and M. Kumada, Bull. Chem. Soc. Jpn., 1980, 53, 1138 CAS.
  15. T. Suzuki, M. Kita, K. Kashiwabara and F. Fujita, Bull. Chem. Soc. Jpn., 1990, 63, 3434 CAS; P. J. Stang, D. H. Cao, S. Siato and A. M. Arif, J. Am. Chem. Soc., 1995, 117, 6273 CrossRef CAS.
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