Phosphonium salts of diacetoxyiodine(I) anions, new reagents for the iodoacetoxylation of alkenes

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

Andreas Kirschning, Claus Plumeier and Lars Rose


Abstract

Novel phosphonium salts of diacetoxyiodine(I) anions 1 add to alkenes like tri-O-benzyl galactal 8 affording 1-acetoxy-2-iodopyranoses 12a,b which can efficiently be employed in the synthesis of 2-deoxyglycoside 14.


References

  1. J. A. Gladysz and J. Boone, Angew. Chem., 1997, 109, 567; Angew. Chem., Int. Ed. Engl., 1997, 36, 551 Search PubMed; J. Rodriguez and J.-P. Dulcère, Synthesis, 1993, 1177 Search PubMed.
  2. J. W. Cornforth and D. T. Green, J. Chem. Soc. (C), 1970, 846 RSC.
  3. L. Mangoni, M. Adinolfi, G. Barone and M. Parrilli, Tetrahedron Lett., 1973, 4485 CrossRef CAS; L. Mangoni, M. Adinolfi, G. Barone and M. Parrilli, Gazz. Chim. Ital., 1975, 105, 377 CAS.
  4. L. Birckenbach, J. Goubeau and E. Berninger, Ber., 1932, 65, 1339 Search PubMed; R. B. Woodward and F. V. Brutcher, Jr., J. Am. Chem. Soc., 1958, 80, 209 CrossRef CAS; R. C. Cambie, D. M. Gash, P. S. Rutledge and P. D. Woodgate, J. Chem. Soc., Perkin Trans. 1, 1977, 1157 RSC; J. Barluenga, M. A. Rodriguez, P. J. Campos and G. Asenio, J. Chem. Soc., Chem. Commun., 1987, 1491 RSC; C. Georgoulis and J. Valery, Bull. Soc. Chim. Fr., 1975, 1431 CAS; R. W. Trainor, G. B. Deacon, W. R. Jackson and N. Giunta, Aust. J. Chem., 1992, 45, 1265 CAS.
  5. M. Adinolfi, M. Parrilli, G. Barone, G. Laonigro and L. Mangoni, Tetrahedron Lett., 1976, 3661 CrossRef CAS.
  6. Iodine(I) complexes were identified with reference to the analogous tetraalkylammonium salts: G. Doleschall and G. Tóth, Tetrahedron, 1980, 36, 1649 Search PubMed; C. Szántay, G. Blaskó, M. Bárczai-Beke, P. Péchy and G. Dörnei, Tetrahedron Lett., 1980, 21, 3509 CrossRef CAS.
  7. These salts are analogues of the Simonini complex [(AcO)2AgI)]: A. Simonini, Monatsn. Chem., 1892, 13, 320 Search PubMed.
  8. J. E. Leffler and L. J. Story, J. Am. Chem. Soc., 1967, 89, 2333 CrossRef CAS.
  9. R. C. Cambie, R. C. Hayward, J. L. Roberts and P. S. Rutledge, J. Chem. Soc., Perkin Trans. 1, 1974, 1858 RSC.
  10. A. Kirschning, A. Bechthold and J. Rohr, Top. Curr. Chem., 1997, 188, 1 CAS; J. F. Kennedy and C. A. White, Bioactive Carbohydrates in Chemistry, Biochemistry, and Biology, Ellis Horwood, Chichester, 1983 Search PubMed; S. J. Danishefsky and M. T. Bilodeau, Angew. Chem., 1996, 108, 1482 Search PubMed; Angew. Chem., Int. Ed. Engl., 1996, 35, 1380.
Click here to see how this site uses Cookies. View our privacy policy here.