Trimethylsilyl chloride-accelerated reduction and pinacol coupling of carbonyl compounds by means of samarium diiodide

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Toshio Honda and Miho Katoh


Abstract

The combination of samarium diiodide (SmI2) and trimethylsilyl chloride (Me3SiCl) in THF–HMPA is found to accelerate the reduction of sterically hindered and enolisable ketones, and also to accelerate pinacolisation of the carbonyl compounds depending on the reaction conditions.


References

  1. J. L. Namy, P. Girard and H. B. Kagan, Nouv. J. Chim., 1977, 1, 5 Search PubMed; P. Girard, J. L. Namy and H. B. Kagan, J. Am. Chem. Soc., 1980, 102, 2693 CrossRef CAS.
  2. H. B. Kagan and J. L. Namy, Tetrahedron, 1986, 42, 6573 CrossRef CAS; J. Inanaga, J. Synth. Org. Chem. Jpn., 1989, 47, 200 Search PubMed; H. B. Kagan, New J. Chem., 1990, 14, 453 Search PubMed; J. A. Soderquist, Aldrichimica Acta, 1991, 24, 15 Search PubMed; G. A. Molander, Chem. Rev., 1992, 92, 29 CrossRef CAS; G. A. Molander and C. R. Harris, Chem. Rev., 1996, 96, 307 CrossRef CAS.
  3. J. Souppe, J. L. Namy and H. B. Kagan, Tetrahedron Lett., 1982, 3497 CrossRef CAS.
  4. J. Inanaga, M. Ishikawa and M. Yamaguchi, Chem. Lett., 1987, 1485.
  5. J. L. Namy, J. Souppe and H. B. Kagan, Tetrahedron Lett., 1983, 24, 765 CrossRef CAS.
  6. F. Machrouhi, B. Hamann, J. L. Namy and H. B. Kagan, Synlett., 1996, 633 CrossRef CAS.
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