Buta-2,3-dienylstannanes, effective reagents for regioselective buta-1,3-dienylation of aldehydes and acetals

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Meiming Luo, Yoshiharu Iwabuchi and Susumi Hatakeyama


Abstract

Two buta-2,3-dienylstannanes, 1-tri-n-butylstannylbuta-2,3-diene and 1-triphenylstannylbuta-2,3-diene, have been prepared and shown to react with aldehydes and acetals under Lewis acid catalyzed conditions producing (buta-1,3-dien-2-yl)methanol derivatives in high yields.


References

  1. For a review on buta-2,3-dienylsilanes, see: S. Hatakeyama, J. Synth. Org. Chem. Jpn., 1997, 55, 793 Search PubMed.
  2. T. Nishiyama, T. Esumi, Y. Iwabuchi, H. Irie and S. Hatakeyama, Tetrahedron Lett., 1998, 39, 43 CrossRef CAS.
  3. B. Zheng and M. Srebnik, J. Org. Chem., 1995, 60, 486 CrossRef CAS; R. Soundararajan, G. Li and H. C. Brown, J. Org. Chem., 1996, 61, 100 CrossRef CAS; B. Zheng and M. Srebnik, Synth. Commun., 1996, 26, 393 CAS.
  4. S. Hatakeyama, M. Yoshida, T. Esumi, Y. Iwabuchi, H. Irie, T. Kawamoto, H. Yamada and M. Nishizawa, Tetrahedron Lett., 1997, 38, 7887 CrossRef CAS.
  5. H. J. Reich, I. L. Reich, K. E. Yelm, J. E. Holladay and D. Gschneidner, J. Am. Chem. Soc., 1993, 115, 6625 CrossRef.
  6. S. Nunomoto and Y. Yamashita, J. Org. Chem., 1979, 44, 4788 CrossRef CAS.
  7. E. Wada, S. Kanemasa, I. Fujiwara and O. Tsuge, Bull. Chem. Soc. Jpn., 1985, 58, 1942 CAS; G. S. Bates, M. D. Fryzuk and C. Stone, Can. J. Chem., 1987, 65, 2612 CAS.
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