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Reaction Phosphite with Acetal Derivatives:Syntheses of 1-Alkoxymethylphosphonates and 1-Alkylthiomethylphosphonates

  • 발행 : 1998.02.20

초록

1-Alkoxymethylphosphonates 4 and 1-alkylthiomethylphosphonates 5 can be prepared by the reaction of actal derivatives and diethyl trimethylsilyl phosphite in the presence of Lewis acid under mild conditions. The dependency of the chemoselectivities with Lewis acid on the reaction of O,S-acetals with phosphites is described.

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참고문헌

  1. Chem. Rev. v.89 Maryanoff, B. E.;Beitz, A. B.
  2. Org. React. v.25 Wadsworth, W. S. Jr.
  3. Organophosphorus Reagents in Organic Synthesis Walker, B. J.;Cadogan, J. I. G.(ed.)
  4. In Comprehensive Organic Synthesis v.1 Kelly, S. E.
  5. Handbook of Organophosphorus Chemistry Mastalerz, P.;Engel, R.(Ed.)
  6. J. Org. Chem. v.35 Corey, E. J.;Shulman, J. I.
  7. J. Org. Chem. v.44 Mikolajczyk, m.;Grzejazczak, S.;Chefczynska, A.;Zaterski, A.
  8. Tetrahedron Lett. v.19 Kluge, A. F.
  9. Liebigs Ann. Chem. v.88 Schaumann, E.;Grabky, F. F.
  10. Org. Proc. Prep. Int. v.21 Farrington, G. K.;Kumar, A.;Wedler, F. C.
  11. Coll. Czech. Chem. Commun. v.54 Holy, A.;rosenberg, I.;Dvorakova, H.
  12. Tetrahedron Lett. v.34 Makomo, H.;Masson, S.;Saquet, M.
  13. Synthesis Burkhouse, D.;Zimmer, H.
  14. Synthesis Mikolajczyk, M.;Balczewski, P.;Grzejszak, S.
  15. Tetrahedron Lett. v.27 Kim, T. H.;Oh, D. Y.
  16. Synth. Commun. v.17 Kim, T. H.;Kim, D. Y.;Oh, D. Y.
  17. Bull Korean Chem. Soc. v.16 Kim, D. Y.;Oh, D. Y.
  18. J. Chem. Soc. Perkin Trans v.1 Kim, D. Y.;Lee, K.;Oh, D. Y.
  19. Synth. Commun. v.16 Kim, D. Y.;Oh, D. Y.
  20. Phosphorus Sulfur v.34 Kim, D. Y.;Kim, T. H.;Oh, D. Y.
  21. Bull. Korean Chem. Soc. v.10 Han, D. I.;Kim, D. Y.;Oh, D. Y.
  22. Phosphorus Sulfur v.28 Lopusinski, A.;Michalski J.;Potrzebowski, M.
  23. J. Chem. Soc. Chem. Commun. Dembinski, R.;Koninski, R.;Michalski, J.;Skowronka, A.
  24. Phosphorus Sulfur v.30 Michalski, J.;Lopusinski, A.;Jezierska, B.;Luczak, L.;Potrzebowski, M.
  25. J. Am. Chem. Soc. v.100 Evans, D. A.;Hurst, K. M.;Takacs, J. M.
  26. J. Org. Chem. v.46 Sekine, M.;Nakajima, M.;Hata, T.
  27. Tetrahedron v.45 Wozniak, L.;Chojnowski, J.
  28. Tetrahedron Lett. v.28 Chemoselective allylation or propargylation with BF₃·OEt₂ and TiCl₄ has been observed in the reaction of O, S-aectals with allyl (or allenyl)tin compounds Sato, T.;Okura, S.;Otera, J.;Nozaki, H.
  29. Synth. Commun. v.7 Ong, B. S.;Chan, T. H.
  30. J. Am. Chem. Soc. v.101 Jensen, J. L.;Jencks, W. P.
  31. Tetrahedron Lett. v.24 Mandi, T.;Hara, K.;Nakajima, J.;Kawada, M.;Otera, J.
  32. J. Org. Chem. v.46 Sekine, M.;Okimota, K.;Yamada, K.;Hata, T.
  33. Angew Chem. Int. Ed. Engl. v.6 Issleib, K.;Walter, B.