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Lithium Trimethylalkynylaluminate, A New Chemoselective Alkynylating Agent

  • 발행 : 1996.04.20

초록

Lithium trimethylalkynylaluminates, prepared conveniently by reacting trimethylaluminum with lithium alkynide, readily react with aldehydes and ketones to give the corresponding propargyl alcohols in 70-95% yields. The reaction is highly chemoselective; thus many other functional groups such as amides, nitriles, epoxides and halogen compounds are inert under the reaction conditions. The reagents also show an excellent 1,2-regiospecificity in the reactions with cyclic or acyclic α,β-unsaturated carbonyl compounds.

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참고문헌

  1. Preparative Acetylenic Chemistry Brandsma, L.
  2. Syntheis Fisch, a.;Coisne, J. M.;Figeys, H. P.
  3. U. S. Pat 3,153,097 v.62 Cameron, M. D.
  4. Tetrahedron Lett. v.25 Corriu, R. J. P.;Huynh, V.;Moreaw, J. J. E.
  5. Organic Syntheses; Coll v.Ⅲ Saunders, J. H.
  6. Organic Sytheses; Coll v.Ⅳ Campbell, K. N.;Campbell, B. K.
  7. Tetrahedron Lett. v.27 Chong, J. M.;Wong, S.
  8. J. Org. Chem. v.54 Delorme, D.;Girard, Y.;Rokach, J.
  9. J. Am. Chem. v.82 Arnold, R. T.;Smolinsky, G.
  10. Synth. Commun v.16 Yamaguchi, M.;Shibato, K.;Fujiwara, S.;Inchiro, H.
  11. Preparative Acetylenic Chemistry Barndsma, L. M.
  12. Rec. Trav. Chim. v.84 Montijn, P. P.;Schmidt, H. M.;van Boom, J. H.;Bos, H. J. T.;Brandsma, L.;Arens, J. F.
  13. Tetrahedron Lett. Capmau, M. L.;Chodkiewicz, W.;Cadiot, P.
  14. J. Chem. Soc. Jones, E. R. H.;Lee, H. H.;Whiting, M. C.
  15. Recl. Trav. Chim. Pays-Bas v.87 Schaap, A.;Arens, J. F.
  16. J. Am. Chem. Soc. v.97 Negishi, E.;Baba, S.
  17. J. Org. Chem. v.41 Danishefsky, S.;Kitahara, T. M.;Tasai, M.;Dynak, J.
  18. J. Am. Chem. Soc. v.93 Hooz. J.;Layton, R. B.
  19. J. Org. Chem. v.60 Ahn, J. H.;Joung, M. J.;Yoon, N. M.
  20. Organic Syntheses; Coll v.Ⅳ Skattebol, L.;Jones, E. R. H.;Whiting M. C.
  21. J. Org. Chem. v.27 Shackelford, J. M.;Michalowicz, W. A.;Schwartzman, L. H.
  22. Synth Commun. v.10 Apsimon, J.;Sequin, R.
  23. J. Org. Chem. v.50 Welch, S. C.;Chon, C. Y.;Gruber, J. M.;Assercq, J.
  24. Organic Syntheses; Coll v.Ⅳ Schaeffer, J. R.;Snody, A. O.