Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Reaction of Lithium 2-Pyridyloxyalkylcuprates Having Improved Thermal Stability with Acid Chlorides and $\alpha,\beta$-Unsaturated Ketones

  • Lee, Phil-Ho (Department of Chemistry, Korea Advanced Institute of Science and Technology) ;
  • Shim, Sang-Chul (Department of Chemistry, Korea Advanced Institute of Science and Technology) ;
  • Kim, Sung-Gak (Department of Chemistry, Korea Advanced Institute of Science and Technology)
  • Published : 1986.12.20
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Abstract

A new heterocuprate containing 2-pyridyloxy ligand, lithium 2-pyridyloxy-n-butylcuprate, has shown improved thermal stability and it reacts with acid chlorides to afford the corresponding ketones in high yields. Similarly, it can be effectively utilized in conjugate addition reactions of $\alpha,\beta$-unsaturated ketones. Of synthetic significance is that the complete utilization of n-butyl group in lithium 2-pyridyloxy-n-butylcuprate has been observed.

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References

  1. Org. React. (N.Y) v.19 G.H. Posner
  2. Org. React. (N.Y) v.22 G.H. Posner
  3. An Introduction to Synthesis Using Organocopper Reagent G.H. Posner
  4. J. Am. Chem. Soc. v.104 S.H. Bertz;G. Dabbagh;G.M. Villacorta
  5. J. Org. Chem. v.49 S.H. Bertz;G. Daggagh
  6. J. Chem. Soc., Chem. Commun. C.R. Johnson;D.S. Dhanoa
  7. J. Org. Chem. v.48 B.H. Lipshutz;D. Parker;J.A. Kozlowski;R.D. Miller
  8. J. Org. Chem. v.46 T. Tsudo;T. Yazawa;K. Watanabe;T. Fujii;T. Saegusa
  9. J. Chem. Soc., Chem. Commun. S.H. Bertz;G. Dabbagh
  10. J. Am. Chem. Soc. v.95 G.H. Posner;C.E. Whitten;J.J. Sterling
  11. Org. React. (N.Y.) v.8 D.A. Shirley
  12. Org. React. (N.Y.) v.18 M.J. Jorgenson
  13. Tetrahedron lett. G.H. Posner;C.E. Whitten
  14. J. Am. Chem. Soc. v.94 G.H. Posner;C.E. Whitten;P.E. McFarland
  15. J. Am. Chem. Soc. v.96 R.J. Anderson;C.A. Henrick;L.D. Rosenblum
  16. J. Chem. Soc., Chem. Commun. S. Kim;J.I. Lee;B.Y. Chung
  17. J. Org. Chem. v.48 S. Kim;J.I. Lee
  18. Tetrahedron Lett. B.H. Lipshutz;R.S. Wilhelm;J. Kozlowski
  19. J. Org. Chem. v.47 Y. Yamamoto;S. Yamamoto;H. Yatagai;Y. Ishinhara;K. Maruyama
  20. Tetrahedron Lett. B.H. Lipshutz;D.A. Parker;J. Kozlowski;S.L. Ngugen

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  1. 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
  2. Regioselective Addition Reactions of the Organoindium Reagents onto α,β-Unsaturated Ketones vol.25, pp.11, 1986, https://doi.org/10.5012/bkcs.2004.25.11.1687
  3. Indium and Gallium-Mediated Addition Reactions vol.28, pp.1, 2007, https://doi.org/10.5012/bkcs.2007.28.1.017