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DOI: 10.1039/A702497E (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 1, 1997, 2023-2032

Direct preparation of diacetals from 1,2-diketones and their use as 1,2-diol protecting groups

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Achim Hense, Steven V. Ley, Helen M. I. Osborn, Dafydd R. Owen, Jean-François Poisson, Stuart L. Warriner and Kieron E. Wesson

Abstract

A range of 1,2-diketones have been evaluated as potential protecting groups for trans-1,2-diols via 1,2-diacetal formation. The procedure is especially useful in oligosaccharide and natural product synthesis.

References

  1. N. L. Douglas, S. V. Ley, H. M. I. Osborn, D. R. Owen, H. W. M. Priepke and S. L. Warriner, Synlett, 1996, 793 CrossRef CAS.
  2. S. V. Ley, H. W. M. Priepke and S. L. Warriner, Angew. Chem., Int. Ed. Engl., 1994, 33, 2290 CrossRef.
  3. P. Grice, S. V. Ley, J. Pietruszka, H. W. M. Priepke and E. P. E. Walther, Synlett, 1995, 783.
  4. P. Grice, S. V. Ley, J. Pietruszka and H. W. M. Priepke, Angew. Chem., Int. Ed. Engl., 1996, 35, 197 CrossRef CAS.
  5. P. Grice, S. V. Ley, J. Pietruszka, H. W. M. Priepke and S. L. Warriner, J. Chem. Soc., Perkin Trans. 1, 1997, 351 RSC.
  6. (a) J.-L. Montchamp, F. Tian, M. E. Hart and J. W. Frost, J. Org. Chem., 1996, 61, 3897 CrossRef CAS; (b) U. Berens, D. Leckel and S. C. Oepen, J. Org. Chem., 1995, 60, 8204 CrossRef CAS.
  7. M. V. Bhatt, Tetrahedron, 1964, 20, 803 CrossRef CAS.
  8. H. D. Durst, M. P. Mack and F. Wudl, J. Org. Chem., 1975, 40, 268 CrossRef CAS.
  9. J. Wrobel and J. M. Cook, Synth. Commun., 1980, 10, 333 CAS.
  10. C. M. Amon, M. G. Banwell and G. L. Gravatt, J. Org. Chem., 1987, 52, 4851 CrossRef CAS.
  11. J. Strating, S. Reiffers and H. Wynberg, Synthesis, 1971, 209 CrossRef CAS.
  12. L. D. Buyck, J. Van Slembrouck, N. De Kimpe, R. Verhe and N. Schamp, Bull. Soc. Chim. Belg., 1984, 93, 913.
  13. Y. Satoh and K. Nishizawa, J. Chem. Soc., Chem. Commun., 1973, 83 RSC.
  14. S. V. Ley, R. Downham, P. J. Edwards, J. E. Innes and M. Woods, Contemp. Org. Synth., 1995, 2, 365 RSC.
  15. M. Bols, Carbohydrate Building Blocks, Wiley-Interscience, New York, 1996, p. 26 Search PubMed.
  16. U. T. Mueller-Westerhoff and M. Zhou, J. Org. Chem., 1994, 59, 4991.
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