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DOI: 10.1039/A903050F (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 1, 1999, 2327-2334

Meisenheimer rearrangements of N-allyl 2-azabornane derivatives

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Jonathan E. H. Buston, Iain Coldham and Keith R. Mulholland

Abstract

A study of the asymmetric [2,3]-Meisenheimer rearrangement of tertiary amine-N-oxides was carried out, in order to provide a method for the preparation of chiral allylic alcohols. The use of 2-azabornane as a chiral auxiliary gives rise to chiral tertiary amine-N-oxides, which undergo the [2,3]-Meisenheimer rearrangement with high levels of stereoselectivity. Reductive N,O-bond cleavage, mediated by ultrasound, of the O-allyl-hydroxylamine allows access to the chiral allylic alcohol.

References

  1. J. Meisenheimer, Chem. Ber., 1919, 52, 1667 Search PubMed.
  2. A. C. Cope and R. F. Kleinschmidt, J. Am. Chem. Soc., 1944, 66, 1929 CrossRef CAS; A. C. Cope and P. H. Towle, J. Am. Chem. Soc., 1949, 71, 3423 CrossRef CAS.
  3. V. Rautenstrauch, Helv. Chim. Acta, 1973, 56, 2492 CAS.
  4. M. Moriwaki, Y. Yamamoto, J. Oda and Y. Inouye, J. Org. Chem., 1976, 41, 303 CrossRef.
  5. M. T. Reetz and E. H. Lauterbach, Tetrahedron Lett., 1991, 32, 4481 CrossRef CAS.
  6. S. G. Davies and G. D. Smyth, Tetrahedron: Asymmetry, 1996, 7, 1001 and 1005 CrossRef CAS.
  7. D. Enders and H. Kempen, Synlett, 1994, 969 CrossRef CAS.
  8. M. Moriwaki, Y. Yamamoto, J. Oda and Y. Inouye, J. Org. Chem., 1976, 41, 300 CrossRef CAS.
  9. J. E. H. Buston, I. Coldham and K. R. Mulholland, Tetrahedron: Asymmetry, 1998, 9, 1995 CrossRef CAS.
  10. J. E. H. Buston, I. Coldham and K. R. Mulholland, Synlett, 1997, 322 CAS.
  11. C. M. Cain, R. P. C. Cousins, G. Coumbarides and N. S. Simpkins, Tetrahedron, 1990, 46, 523 CrossRef CAS.
  12. P. G. Gassman and K. Shudo, J. Am. Chem. Soc., 1971, 93, 5899 CrossRef CAS.
  13. S. Oae and H. Togo, Synthesis, 1981, 371 CrossRef CAS.
  14. B. E. Love and J. Ren, J. Org. Chem., 1993, 58, 5556 CrossRef CAS.
  15. A related isomer of amine 1 R = H has been prepared subsequently by S. M. Starling, S. C. Vonwiller and J. N. H. Reek, J. Org. Chem., 1998, 63, 2262 Search PubMed.
  16. R. K. Boeckman, S. G. Nelson and M. D. Gaul, J. Am. Chem. Soc., 1992, 114, 2258 CrossRef.
  17. F. A. Davis, Org. Synth., 1988, 66, 203.
  18. A. C. Cope and E. R. Trumbull, Org. React., 1960, 11, 317 CAS.
  19. D. A. Forsyth, W. Zhang and J. A. Hanley, J. Org. Chem., 1996, 61, 1284 CrossRef CAS.
  20. G. Ohloff and E. Klein, Tetrahedron, 1962, 18, 37 CrossRef CAS.
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