Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

A Facile Preparation of 2-(2-Hydroxyethyl)homoallenylsilanes Using In Situ Generated Homoallenylindium Reagent

  • Published : 20011200
Download PDF
⟨ Previous Next ⟩

Abstract

In situ generated homoallenylindium reagents derived from the reaction of indium with 4-bromo-3-[(tri-methylsilyl) methyl]-1,2-butadiene reacted with a variety of aldehydes in DMF to produce 2-(2-hydroxy-ethyl) homoallenylsilanes at room temperatu re in good to excellent yields. 2- or 3-Hydroxybenzaldehyde that contains labile hydrogen was reacted with homoallenylindium reagent to provide the homoallenylsilanes. In the case of 4-formylbenzoic acid, the desired compound was produced in 88% yield. 4-Bromo-3-[(trimethyl-silyl) methyl]-1,2-butadiene was prepared from monoacetylation and mesylation of 2-butyn-1,4-diol, addition of trimethylsilylmethyl anion, saponification and mesylation followed by Finkelstein reaction.

Keywords

References

  1. Chem. Rev. v.93 Yamamoto, Y.;Asao, N.
  2. Tetrahedron Lett. v.15 Gardillo, G.;Contento, M.;Sandri, S.
  3. Tetrahedron Lett. v.19 Sarkar, T. K.;Andersen, N. H.
  4. Chem. Pharm. Bull. v.31 Ochiai, M.;Fujita, E.;Arimoto, M.;Yamaguchi, H.
  5. Tetrahedron Lett. v.26 Gramain, J.-C.; Remuson, R.
  6. Tetrahedron Lett. v.23 Nishiyama, H.;Yokoyama, H.;Narimatsu, S.;Itoh, K.
  7. Tetrahedron Lett. v.35 Blanco, F. J.;Cuadrado, P.;Gonzalez, A. M.;Pulido, F. J.;Fleming, I.
  8. Synlett v.37 Bardot, V.;Remuson, R.;Gelas-Mialhe, Y.;Gramain, J.
  9. Tetrahedron v.52 Li, C.-J.
  10. Organic Reactions in Aqueous Media Li, C.-J.;Chan, T.-H.
  11. Chem. Rev. v.93 Li, C.-J.
  12. Tetrahedron v.55 Li, C.-J.;Chan, T.-H.
  13. Tetrahedron Lett. v.32 Li, C.-J.;Chan, T.-H.
  14. Tetrahedron Lett. v.36 Isaac, M. B.;Chan, T.-H.
  15. Tetrahedron Lett. v.33 Beuchet, P.;Marrec, N. L.;Mosset, P.
  16. Tetrahedron Lett. v.38 Loh, T.-P.;Ho, D. S.;Xu, K.-C.;Sim, K.-Y.
  17. Tetrahedron Lett. v.39 Chan, T.-H.;Lu, W.
  18. J. Am. Chem. Soc. v.118 Li, C.-J.;Chen, D.-L.;Lu, Y.-Q.;Haberman, X.;Mague, J. T.
  19. Tetrahedron Lett. v.38 Haberman, J. X.;Li, C.-J.
  20. Tetrahedron v.54 Li, C.-J.;Chen, D.-L.;Lu, Y.-Q.;Haberman, X.;Mague, J. T.
  21. Tetrahedron Lett. v.40 Yang, J.;Viswanathan, G. S.
  22. Org. Lett. v.1 Viswanathan, G. S.;Yang, J.;Li, C.-J.
  23. Tetrahedron Lett. v.37 Bryan, V. J.;Chan, T.-H.
  24. Tetrahredron Lett. v.42 Lee, P. H.;Ahn, H.;Lee, K.;Sung, S.-Y.;Kim, S.
  25. Synth. Commun. v.31 Lee, P. H.;Lee, K.;Chang, S.
  26. Org. Lett. v.3 Lee, P. H.;Lee, K.; Kim, S.
  27. Org. Lett. v.3 Lee, P. H.;Sung, S.-Y.; Lee, K.
  28. Tetrahredron Lett. v.41 For a preliminary account of this work Lee, P. H.;Bang, K.;Lee, K.;Lee, C.-H.;Chang, S.

Cited by

  1. Sonochemical Reformatsky Reaction Using Indium vol.23, pp.9, 2001, https://doi.org/10.5012/bkcs.2002.23.9.1272
  2. ChemInform Abstract: A Facile Preparation of 2-(2-Hydroxyethyl)homoallenylsilanes Using in situ Generated Homoallenylindium Reagent. vol.33, pp.28, 2001, https://doi.org/10.1002/chin.200228214
  3. Indium-Mediated &bgr;-Allylation, &bgr;-Propargylation, and &bgr;-Allenylation onto &agr;,&bgr;-Unsaturated Ketones: Reactions of in-Situ-Generated 3-tert-Butyldimethylsilyloxyalk-2-enylsulfonium Sal vol.125, pp.32, 2003, https://doi.org/10.1021/ja035988m
  4. Palladium-Catalyzed Homocoupling Reaction of 1-Iodoalkynes: A Simple and Efficient Synthesis of Symmetrical 1,3-Diynes vol.68, pp.18, 2001, https://doi.org/10.1021/jo034727s
  5. Regioselective Addition Reactions of the Organoindium Reagents onto α,β-Unsaturated Ketones vol.25, pp.11, 2001, https://doi.org/10.5012/bkcs.2004.25.11.1687
  6. Regioselective allylgallation of terminal alkynes vol.2005, pp.14, 2005, https://doi.org/10.1039/b417975g
  7. Indium and Gallium-Mediated Addition Reactions vol.28, pp.1, 2007, https://doi.org/10.5012/bkcs.2007.28.1.017
  8. Synthesis of a Naturally Occurring Diene-Containing Amino Acid and Its Glutamyl Dipeptide via N-Acyliminium Ion Chemistry vol.2008, pp.5, 2008, https://doi.org/10.1002/ejoc.200701016
  9. Intermolecular Double Prins-Type Cyclization: A Facile and Efficient Synthesis of 1,6-Dioxecanes vol.121, pp.12, 2001, https://doi.org/10.1002/ange.200804576
  10. Intermolecular Double Prins-Type Cyclization: A Facile and Efficient Synthesis of 1,6-Dioxecanes vol.48, pp.12, 2009, https://doi.org/10.1002/anie.200804576
  11. Synthesis of 3,4-Dimethylidene Oxacycles through Prins-Type Cyclization of Allenylmethylsilanes vol.6, pp.8, 2001, https://doi.org/10.1002/asia.201100162
  12. Palladium-Catalyzed Cross-Coupling Reaction and Gold-Catalyzed Cyclization for Preparation of Ethyl 2-Aryl 2,3-Alkadienoates and α-Aryl γ-Butenolides vol.32, pp.8, 2001, https://doi.org/10.5012/bkcs.2011.32.8.2911
  13. Organoindium Reagents: The Preparation and Application in Organic Synthesis vol.113, pp.1, 2001, https://doi.org/10.1021/cr300051y