Bulletin of the Korean Chemical Society

  • 제22권12호
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  • Pages.1385-1389
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  • 2001
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  • 0253-2964(pISSN)
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  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
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A Facile Preparation of 2-(2-Hydroxyethyl)homoallenylsilanes Using In Situ Generated Homoallenylindium Reagent

  • 발행 : 20011200
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초록

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.

키워드

참고문헌

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피인용 문헌

  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