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DOI: 10.1039/A803739F (Paper) Reference Section for: J. Chem. Soc., Dalton Trans., 1998, 3727-3730

Resolution of a cyclopalladated ferrocenylketimine

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Yang Jie Wu, Xiu Ling Cui, Chen Xia Du, Wen Ling Wang, Rui Yun Guo and Rong Feng Chen

Abstract

The cyclopalladated ferrocenylketimine, [{Pd[(η5-C5H5)Fe{η5-C5H3C(CH3)[double bond, length half m-dash]N(C6H4CH3-4)}](µ-Cl)}2] 1 was resolved into optically active diastereomers by using (S[hair space])-leucine as chiral auxiliary. The new optically active (S[hair space])-leucinato complexes of PdII containing ferrocenylketimine could be converted into optically active dimers with the same absolute configurations in the ferrocene moiety. The structure of the chiral dimer (Rp,Rp)-1 was determined by X-ray diffraction, on the basis of which the absolute configurations of all the optically active compounds studied were ascertained.

References

  1. M. I. Bruce, Angew. Chem., Int. Ed. Engl., 1977, 16, 73 CrossRef ; C. H. Chao, D. W. Hast, R. Bau and R. F. Heck, J. Organomet. Chem., 1979, 179, 301 CrossRef CAS ; N. Beydoun and M. Pfeffer, Synthesis, 1990, 729 CrossRef CAS ; M. Pfeffer, J. P. Sutter, A. Decian and J. Fischer, Organometallics, 1993, 12, 1167 CrossRef CAS .
  2. S. Y. M. Chooi, P. H. Leung, C. C. Lim, K. F. Mok, G. H. Quek, K. Y. Sim and M. K. Tam, Tetrahedron: Asymmetry, 1992, 3, 529 CrossRef CAS ; S. Y. M. Chooi, S. Y. Siah, P. H. Leung and K. F. Mok, Inorg. Chem., 1993, 32, 4812 CrossRef CAS ; J. L. Bookham and W. Mcfarlane, J. Chem. Soc., Chem. Commun., 1993, 1352 RSC ; D. G. Allen, G. M. Mclaughlin, G. B. Robertson, W. L. Steffen, G. Salem and S. B. Wild, Inorg. Chem., 1982, 21, 1007 CrossRef CAS ; R. T. Aplin, H. Doucet, M. W. Hooper and J. M. Brown, Chem. Commun., 1997, 2097 RSC .
  3. V. I. Sokolov, L. L. Troitskaya and O. A. Reatov, J. Organomet. Chem., 1979, 182, 537 CrossRef CAS ; T. Hayashi and M. Kumada, Asymmetric Synthesis, Academic Press, Inc., Orlando, FL, 1985, vol. 5, p. 147 Search PubMed ; A. Togni and T. Hayashi, Ferrocenes: Homogeneous Catalysis, Organic Synthesis and Materials Science, VCH, Weinheim, 1995, p. 105 and refs. therein Search PubMed ; K. H. Ahn, C. W. Cho, H. H. Baek, J. Park and S. Lee, J. Org. Chem., 1995, 61, 4937 Search PubMed .
  4. T. Komatsu, M. Nonoyama and J. Fujita, Bull. Chem. Soc. Jpn., 1981, 54, 184 .
  5. V. I. Sokolov, L. L. Troitskaya and O. A. Reatov, J. Organomet. Chem., 1977, 133, C28 CrossRef CAS .
  6. A. Patti, D. Lambusta, M. Piattelli and G. Nicolosi, Tetrahedron, 1997, 53, 1361 CrossRef CAS .
  7. (a) S. Q. Huo, Y. J. Wu, C. X. Du, H. Z. Yuan and X. A. Mao, J. Organomet. Chem., 1994, 483, 139 CrossRef CAS ; (b) Y. J. Wu, Y. H. Liu, H. Z. Yuan and X. A. Mao, Polyhedron, 1996, 15, 3315 CrossRef CAS ; (c) C. López, J. Sales, X. Solans and R. Zquiak, J. Chem. Soc., Dalton Trans., 1992, 2321 RSC .
  8. R. Navarro, J. Garcia, E. P. Urriolabeitia, C. Catviela and M. D. Diaz-de-Villegas, J. Organomet. Chem., 1995, 490, 35 CrossRef CAS .
  9. J. C. Gaunt and B. L. Shaw, J. Organomet. Chem., 1975, 102, 511 CrossRef CAS ; A. Kasahara, T. Izumi and M. Maemura, Bull. Chem. Soc. Jpn., 1977, 50, 1878 CAS .
  10. K. Schlögl, M. Fried and H. Falk, Monatsh. Chem., 1964, 95, 576 .
  11. SIR 92, A. Altomare, M. C. Burla, M. Camalli, M. Cascarano, C. Giacovazzo, A. Guagliardi and G. Polidori, J. Appl. Crystallogr., 1994, 27, 435 Search PubMed .
  12. W. C. Hamilton, Acta Crystallogr., 1965, 18, 502 CrossRef CAS .
  13. TEXSAN, Crystal Structure Analysis Package, Molecular Structure Corporation, Houston, TX, 1985 and 1992 .
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