View PDF Version
 
DOI: 10.1039/A903805A (Paper) Reference Section for: Chem. Commun., 1999, 1437-1438

Ruthenium-catalysed multiple component transformations: one-step stereoselective synthesis of functional dienes from alkynes and carboxylic acids

(Note: The full text of this document is currently only available in the PDF Version )

Jacques Le Paih, Sylvie Dérien and Pierre H. Dixneuf

Abstract

The precatalyst RuCl(cod)C5Me5 allows the head-to-head oxidative dimerization of terminal alkynes and the concommittent 1,4-addition of carboxylic acid to afford (1E,3E)-1-acyloxy-1,3-dienes in one step under mild conditions.

References

  1. I. Ugi, Angew. Chem., 1962, 74, 9 CAS; A. Dömling and I. Ugi, Angew. Chem., Int. Ed. Engl., 1993, 32, 563 CrossRef.
  2. L. F. Tietze and U. Beifuss, Angew. Chem., 1993, 105, 137 CrossRef CAS; L. F. Tietze and U. Beifuss, Angew. Chem., Int. Ed. Engl., 1993, 32, 131 CrossRef; G. H. Posner, Chem. Rev., 1986, 86, 831 CrossRef CAS; B. M. Trost, Angew. Chem., Int. Ed. Engl., 1995, 34, 259 CrossRef CAS.
  3. Y. Yamamoto, H. Kitahara, R. Hattori and K. Itoh, Organometallics, 1998, 17, 1910 CrossRef CAS.
  4. N. Chatani, Y. Fukumoto, T. Ida and S. Murai, J. Am. Chem. Soc., 1993, 115, 11614 CrossRef CAS.
  5. T. Morimoto, N. Chatani, Y. Fukumoto and S. Murai, J. Org. Chem., 1997, 62, 3762 CrossRef CAS; T. Kondo, N. Suzuki, T. Okada and T. Mitsudo, J. Am. Chem. Soc., 1997, 119, 6187 CrossRef CAS.
  6. N. Suzuki, T. Kondo and T. Mitsudo, Organometallics, 1998, 17, 766 CrossRef CAS.
  7. N. Chatani, Y. Ie, F. Kakiuchi and S. Murai, J. Org. Chem., 1997, 62, 2604 CrossRef CAS; E. J. Moore, W. R. Pretzer, T. J. O'Connell, J. Harris, L. LaBounty, L. Chou and S. S. Grimmer, J. Am. Chem. Soc., 1992, 114, 5888 CrossRef CAS.
  8. B. M. Trost, M. Portnoy and H. Kurihara, J. Am. Chem. Soc., 1997, 119, 836 CrossRef CAS.
  9. B. M. Trost and A. B. Pinkerton, J. Am. Chem. Soc., 1999, 121, 1988 CrossRef CAS.
  10. C. S. Yi, J. R. Torres-Luhian, N. Liu, A. L. Rheingold and I. A. Guzei, Organometallics, 1998, 17, 1257 CrossRef CAS.
  11. S. Dérien, D. Jan and P. H. Dixneuf, Tetrahedron, 1996, 52, 5511 CrossRef CAS.
  12. S. Dérien, L. Ropartz, J. Le Paih and P. H. Dixneuf, J. Org. Chem., 1999, 64, 3524 CrossRef CAS; S. Dérien, B. Gomez-Vicente and P. H. Dixneuf, Chem. Commun., 1997, 1405 RSC.
  13. M. O. Albers, D. J. A. de Waal, D. C. Liles, D. J. Robinson, E. Singleton and M. B. Wiege, J. Chem. Soc., Chem. Commun., 1986, 1680 RSC.
  14. C. Gemel, A. La Pensée, K. Mauthner, K. Mereiter, R. Schmid and K. Kirchner, Monatsh. Chem., 1997, 128, 1189 CAS.
  15. H. Le Bozec, J.-L. Fillaut and P. H. Dixneuf, J. Chem. Soc., Chem. Commun., 1986, 1182 RSC; V. A. Osborn, A. Craig and M. J. Winter, J. Chem. Soc., Chem. Commun., 1986, 1185 RSC.
Click here to see how this site uses Cookies. View our privacy policy here.