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DOI: 10.1039/A803494J (Paper) Reference Section for: Chem. Commun., 1998, 1557-1558

Catalytic asymmetric imidation of selenides into selenimides

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Hiroya Takada, Yoshihiro Miyake, Kouichi Ohe and Sakae Uemura

Abstract

The direct catalytic imidation of various prochiral selenides with TsN[double bond, length half m-dash]IPh in the presence of CuOTf using chiral 4,4′-disubstituted 2,2′-bis(oxazoline) ligand afforded the corresponding chiral selenimides (∼36% ee).

References

  1. See for example: Sulfur Reagents in Organic Synthesis, ed. P. Metzner and A. Thuillier, Academic Press, London, 1994 Search PubMed.
  2. Y. Yamada, T. Yamamoto and M. Okawara, Chem. Lett., 1975, 361 CAS.
  3. H. Takada, Y. Nishibayashi, K. Ohe and S. Uemura, Chem. Commun., 1996, 931 RSC; H. Takada, Y. Nishibayashi, K. Ohe, S. Uemura, C. P. Baird, T. J. Sparey and P. C. Taylor, J. Org. Chem., 1997, 62, 6512 CrossRef CAS; H. Takada, Y. Nishibayashi, K. Ohe and S. Uemura, Phosphorus Sulfur Silicon Relat. Elem., 1997, 120–121, 363.
  4. V. P. Krasnov, V. I. Naddaka and V. I. Minkin, Zh. Org. Khim., 1981, 17, 445 CAS; Chem. Abstr., 1981, 95, 42551x Search PubMed.
  5. F. A. Davis, J. M. Billmers and O. D. Stringer, Tetrahedron Lett., 1983, 24, 3191 CrossRef CAS.
  6. T. Shimizu, N. Seki, H. Taka and N. Kamigata, J. Org. Chem., 1996, 61, 6013 CrossRef CAS; T. Shimizu and N. Kamigata, Org. Prep. Proced. Int., 1997, 29, 603 CrossRef CAS.
  7. T. Shimizu, K. Kikuchi, Y. Ishikawa, I. Ikemoto, M. Kobayashi and N. Kamigata, J. Chem. Soc., Perkin Trans. 1, 1989, 597 RSC.
  8. Y. Nishibayashi, T. Chiba, K. Ohe and S. Uemura, J. Chem. Soc., Chem. Commun., 1995, 1243 RSC.
  9. Toluene was also revealed to be the solvent of choice for asymmetric sulfimidation of organic sulfides.3.
  10. Excess selenide was employed (2.0 equiv.) and TsN[double bond, length as m-dash]IPh served as the limiting reagent.
  11. S. Tamagaki, S. Oae and K. Sakaki, Tetrahedron Lett., 1975, 649 CrossRef CAS.
  12. F. A. Davis and R. T. Reddy, Tetrahedron, 1985, 41, 4747 CrossRef CAS; K. B. Sharpless, M. W. Young and R. F. Lauer, Tetrahedron Lett., 1973, 1979 CrossRef CAS; M. Oki and H. Iwamura, Tetrahedron Lett., 1966, 2917 CrossRef; W. J. Burlant and E. S. Gould, J. Am. Chem. Soc., 1954, 76, 5775 CrossRef CAS; T. W. Campbell, H. G. Walker and G. M. Coppinger, Chem. Rev., 1952, 50, 297; R. W. Gaithwaite, J. Kenyon and H. Phillips, J. Chem. Soc., 1928, 2080 Search PubMed.
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