Chiral ruthenium complexes as catalysts in enantioselective Diels–Alder reactions. Crystal structure of the Lewis acid–dienophile adduct

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Daniel Carmona, Sergio Elipe, Fernando J. Lahoz, Luis A. Oro, Carlos Cativiela, M. Pilar López-Ram de Víu, M. Pilar Lamata, Cristina Vega and Fernando Viguri


Abstract

On the basis of spectroscopic and structural studies a full catalytic cycle is proposed for the Diels–Alder reaction between methacrolein and cyclopentadiene when the new chiral aquo-complexes (RRu, SRu)-[(η6-p-cymene)Ru(PN)(H2O)][SbF6]2 {PN = (3aS, 8aR)-2-(2-diphenylphosphinophenyl)-3a,8a-dihydroindane[1,2-d]oxazole} are used as catalysts.


References

  1. W. Carruthers, Cycloaddition Reactions in Organic Synthesis, Pergamon, New York, 1990, p. 1 Search PubMed.
  2. H. B. Kagan and O. Riant, Chem. Rev., 1992, 92, 1007 CrossRef CAS.
  3. S. Kobayashi and H. Ishitani, J. Am. Chem. Soc., 1994, 116, 4083 CrossRef CAS; E. P. Kündig, B. Bourdin and G. Bernardinelli, Angew. Chem., Int. Ed. Engl., 1994, 33, 1856 CrossRef; D. A. Evans, J. A. Murry, P. von Matt, R. D. Norcross and S. J. Miller, ibid., 1995, 34, 798 Search PubMed; J. Jaquith, J. Guan, S. Wang and S. Collins, Organometallics, 1995, 14, 1079 CrossRef CAS; S.-Y. Siah, P.-H. Leung and K. F. Mok, J. Chem. Soc., Chem. Commun., 1995, 1747 RSC.
  4. S. Shambayati, W. E. Crowe and S. L. Schreiber, Angew. Chem., Int. Ed. Engl., 1990, 29, 256 CrossRef; K. V. Gothelf, R. G. Hazell and K. A. Jorgensen, J. Am. Chem. Soc., 1995, 117, 4435 CrossRef CAS.
  5. D. Carmona, C. Cativiela, R. García-Correas, F. J. Lahoz, M. P. Lamata, J. A. López, M. P. López-Ram de Víu, L. A. Oro, E. San José and F. Viguri, Chem. Commun., 1996, 1247 RSC and references therein.
  6. J. V. Allen, G. J. Dawson, C. G. Frost, J. M. J. Williams and S. J. Coote, Tetrahedron, 1994, 50, 799 CrossRef CAS.
  7. K. Stanley and M. C. Baird, J. Am. Chem. Soc., 1975, 97, 6598 CrossRef CAS; T. E. Sloan, Top. Stereochem., 1981, 12, 1 Search PubMed.
  8. G. M. Sheldrick, SHELXS-86, A program for Crystal Structure Solution, University of Göttingen, 1990; G. M. Sheldrick, SHELXL-93, A program for Crystal Structure Refinement, University of Göttingen, 1993.
  9. K. Furuta, S. Shimizu, Y. Miwa and H. Yamamoto, J. Org. Chem., 1989, 54, 1481 CrossRef CAS.
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