Synthesis of homoallylic (but-3-enylic) alcohols from aldehydes with allylic chlorides, tin(II) chloride and potassium iodide in water

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Didier Houllemare, Francis Outurquin and Claude Paulmier


Abstract

Homoallylic (but-3-enylic) alcohols have been prepared in good yields by reductive allylation of aldehydes in water with various allylic chlorides in the presence of tin(II) chloride and potassium iodide. The Barbier type reaction with prop-2-ynyl chloride is also achieved under the same conditions.


References

  1. Y. Yamamoto and N. Asao, Chem. Rev., 1993, 93, 2207 CrossRef CAS.
  2. D. Houllemare, F. Outurquin and C. Paulmier, unpublished results.
  3. Reviews for Barbier type allylations in aqueous media: C. J. Li, Chem. Rev., 1993, 93, 2023 Search PubMed; T. H. Chan, C. J. Li, M. C. Lee and Z. Y. Wei, Can. J. Chem., 1994, 72, 1181 CrossRef CAS; C. J. Li, Tetrahedron, 1996, 52, 5643 CAS; P. Cintas, Synlett, 1995, 1087 CrossRef CAS.
  4. C. Petrier, J. Einhorn and J. L. Luche, Tetrahedron Lett., 1985, 26, 1449 CrossRef.
  5. H. Yamataka, K. Nishikawa and T. Hanafusa, Bull. Chem. Soc. Jpn., 1992, 65, 2145 CAS.
  6. T. Mukaiyama, T. Harada and S. Shoda, Chem. Lett., 1980, 1507 CAS.
  7. (a) T. Imai and S. Nishida, Synthesis, 1993, 395 CrossRef CAS; (b) T. Imai and S. Nishida, J. Chem. Soc., Chem. Commun., 1994, 277 RSC.
  8. K. Uneyama, N. Kamaki, A. Moriya and S. Torii, J. Org. Chem., 1985, 50, 5396 CrossRef CAS; K. Uneyama, K. Ueda and S. Torii, Chem. Lett., 1986, 1201 CAS; P. Talaga, M. Schaeffer, C. Benezra and J. L. Stampf, Synthesis, 1989, 530.
  9. Y. Masuyama, M. Kishida and Y. Kurusu, Tetrahedron Lett., 1996, 37, 7103 CrossRef CAS.
  10. Tin salts of general formula: Et4N+SnX2Y have been prepared but their aqueous solutions were not studied; R. J. H. Clark, L. Maresca and P. J. Smith, J. Chem. Soc. (A), 1970, 2687 Search PubMed.
  11. D. Furlani, D. Marton, G. Tagliavini and M. Zordan, J. Organomet. Chem., 1988, 341, 345 CrossRef CAS.
  12. S. Kobayashi and K. Nishio, J. Org. Chem., 1994, 59, 6620 CrossRef CAS.
  13. D. Marton, D. Stivanello and G. Tagliavini, J. Org. Chem., 1996, 61, 2731 CrossRef CAS.
  14. T. Mukaiyama and T. Harada, Chem. Lett., 1981, 621 CAS.
  15. J. N. Fitzner, D. V. Pratt and P. B. Hopkins, Tetrahedron Lett., 1985, 26, 1959 CrossRef CAS.
  16. J. Drouin, F. Leyendecker and J. M. Conia, Tetrahedron, 1980, 36, 1195 CrossRef CAS.
  17. R. Antonioletti, M. D'Auria, M. de Mico, G. Piancatelli and A. Scettri, Synthesis, 1983, 890 CrossRef CAS.
  18. J. Wulff and R. Huisgen, Chem. Ber., 1969, 102, 1841 CAS.
  19. Y. Oda, S. Matsuo and K. Saito, Tetrahedron Lett., 1992, 33, 97 CrossRef CAS.
  20. S. K. Kang, D. Y. Kim, R. K. Hong and P. S. Ho, Synth. Commun., 1996, 26, 1493 CrossRef CAS.
  21. Y. P. Takahara, Y. Masuyama and Y. Kurusu, J. Am. Chem. Soc., 1992, 114, 2577 CrossRef CAS.
  22. J. Y. Zhou, X. B. Yao, Z. G. Chen and S. H. Wu, Synth. Commun., 1995, 25, 3081 CAS.
  23. K. Ishihara, M. Mouri, Q. Gao, T. Maruyama, K. Furuta and H. Yamamoto, J. Am. Chem. Soc., 1993, 115, 11490 CrossRef CAS.
  24. T. Imai and S. Nishida, Synthesis, 1993, 395 CrossRef CAS.
  25. C. Jubert and P. Knochel, J. Org. Chem., 1992, 57, 5425 CrossRef CAS.
  26. E. Montaudon, J. Thépénier and R. Lalande, J. Heterocycl. Chem., 1979, 16, 113 CAS.
  27. C. H. Heathcock, S. I. Kiyooka and T. A. Blumenkopf, J. Org. Chem., 1984, 49, 4214 CrossRef CAS.
  28. G. P. Boldrini, D. Savoia, E. Tagliavini, C. Trombini and A. Umani-Ronchi, J. Organomet. Chem., 1985, 280, 307 CrossRef CAS.
  29. C. Sarangi, N. B. Das and R. P. Sharma, J. Chem. Res. (S), 1994, 398 Search PubMed.
  30. S. Kim and S. H. Kim, Tetrahedron Lett., 1995, 36, 3723 CrossRef CAS.
  31. A. Yanagisawa, H. Inoue, M. Morodome and H. Yamamoto, J. Am. Chem. Soc., 1993, 115, 10356 CrossRef CAS.
  32. S. Araki, H. Ito and Y. Butsugan, J. Organomet. Chem., 1988, 347, 5 CrossRef CAS.
  33. N. Ikeda, I. Arai and H. Yamamoto, J. Am. Chem. Soc., 1986, 108, 483 CrossRef CAS.
  34. S. Searles, Y. Li, B. Nassim, M. T. Robert Lopes, P. T. Tran and P. Crabbé, J. Chem. Soc., Perkin Trans. 1, 1984, 747 RSC.
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