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Convenient Synthesis of 20(Chloromethyl)-3-(trimethylsilyl)propene and Allylsilane Based Bifunctional Reagents


Abstract

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References

  1. Angew. Chem. Int. Ed. Engl. v.25 Trost, B.M.
  2. Tetrahedron Lett v.27 Molander, G.A.;Shubert, D.C.
  3. Synlett D'Aniello, F.;Mattii, D.;Taddei, M.
  4. Tetrahedron v.49 Ramon, D.J.;Yus, M.
  5. Tetrahedron Lett v.27 Knapp, S.;O'Connor, U.;Mobilio, D.
  6. Org. Syn. v.62 Trost, B.M.;Chan, D.M.;Nanninga, T.N.
  7. Tetrahedron Lett v.29 Lee, T.V.;Porter, J.R.;Roden, F.S.
  8. J. Org. Chem. v.53 Trost, B.M.;Bach, M.;Miller, M.L.
  9. J. Am. Chem. Soc. v.75 Gragson, J.T.;Greenlee, K.W.;Derfer, J.M.;Boord, C.E.
  10. J. Am. Chem. Soc. v.109 The intermediacy of 3-(trifluorostannyl)-2-(trimethylsilylmethyl)propene was reported in the reaction of the iodide 1c with stannous fluoride Molander, G.A.;Shubert, D.C.
  11. Tetrahedron Lett v.33 Kang, K.T.;Lee, J.C.;U, J.S.
  12. Tetrahedron Lett. v.33 Kang, K.T.;Kim, S.S.;Lee, J.C.;U, J.S.
  13. Tetrahedron Lett. v.32 Kang, K.T.;Kim, S.S.;Lee, J.C.
  14. J. Org. Chem. v.53 Xiao, X.;Park, S.K.;Prestwich, G.D.
  15. Tetrahedron Lett. v.22 The iodide 1c was reported to prepare from tje mesylate(1, x=Ms) Trost, B.M.;Curran, D.P.

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  1. Synthesis of Functionalized Allylsilanes Using 3-(Stannyl)-2-(silylmethyl)propene vol.27, pp.7, 1995, https://doi.org/10.1080/00397919708003354
  2. Regioselective synthesis of 2,4-disubstituted thiophenes vol.28, pp.3, 1995, https://doi.org/10.1080/02678290010011599
  3. Synthesis of 4-Alkylfuran-2-acetates and 4-Alkylthiophene-2-acetates Using 2-(Chloromethyl)-3-(tributylstannyl)propene vol.23, pp.9, 2002, https://doi.org/10.5012/bkcs.2002.23.9.1333
  4. Facile Synthesis of Various 1-Azabicyclo[n.4.0]alkanes via Beckmann Rearrangement/Allylsilane Cyclization vol.29, pp.9, 1995, https://doi.org/10.5012/bkcs.2008.29.9.1669
  5. 1,3-Bifunctional Nucleophilic Allylation Reagents: Preparative Methods and Synthetic Applications vol.53, pp.13, 1995, https://doi.org/10.1055/a-1389-1438