Stereoselective Synthesis of 1,4-Dienes through Sequential Cross Coupling of (E)-α-Selanylvinylstannanes†

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

Yun Ma and Xian Huang


Abstract

(E)-α-Selanylvinylstannanes underwent palladium-catalysed coupling reaction with allyl bromides to give 1,4-dienyl selenides; the products can react with Grignard reagent to afford 1,4-dienes in the presence of Ni(dppp)2Cl2.


References

  1. B. H. Lipshut, R. Kell and J. C. Barton, Tetrahedron Lett., 1992, 33, 5861 CrossRef CAS.
  2. H. Imanieh, D. Madeod, P. Quayle and Y. Zhao, Tetrahedron Lett., 1992, 33, 405 CrossRef CAS.
  3. A. Degl Innocenti, P. Ulivi and G. Reginato, Synlett, 1992, 883 CrossRef.
  4. H. Imanieh, Tetrahedron Lett., 1992, 33, 405 CrossRef CAS.
  5. C. E. Tucker and P. Knochel, J. Am. Chem. Soc., 1991, 113, 9888 CrossRef CAS.
  6. T. Yoshida and E. Negishi, J. Am. Chem. Soc., 1981, 103, 1276 CrossRef CAS.
  7. X. Huang and Y. Ma, Synthesis, 1997, 4, 417 CrossRef.
  8. M. Pereyre, J. P. Quintard and A. Rahm, Tin in Organic Synthesis, Butterworths, London, 1987 Search PubMed.
  9. J. K. Stille, Angew. Chem., Int. Ed. Engl., 1986, 25, 508 CrossRef.
  10. J. V. Comasseto, J. Organomet. Chem., 1983, 258, 131 CrossRef CAS.
Click here to see how this site uses Cookies. View our privacy policy here.