Regio- and Stereo-chemical Effects in the Hydroboration ofΔ2 -Steroidal Allylic and HomoallylicAlcohols†

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James R. Hanson, Mansur D. Liman and Sivajini Nagaratnam


Abstract

A comparison between the hydroboration ofΔ2 -steroidal 1α-allylic and5α-homoallylic alcohols reveals that whereas both have astereochemical directing effect, only the allylic alcoholmodifies the regiospecificity of the reaction.


References

  1. H. C. Brown and K. A. Keblys, J. Am. Chem. Soc., 1964, 86, 1791 CrossRef CAS.
  2. H. C. Brown and O. J. Cope, J. Am. Chem. Soc., 1964, 86, 1801 CrossRef CAS.
  3. H. C. Brown and R. M. Gallivan, J. Am. Chem. Soc., 1968, 90, 2906 CrossRef CAS.
  4. E. Dunkelblum, R. Levene and J. Klein, Tetrahedron, 1972, 28, 1009 CrossRef CAS.
  5. J. R. Hanson, P. B. Hitchcock, M. Liman and S. Nagaratnam, J. Chem. Soc., Perkin Trans. 1, 1995, 2183 RSC.
  6. M. Alam, J. R. Hanson, M. Liman and S. Nagaratnam, J. Chem. Res. (S), 1997, 56 RSC.
  7. G. C. Wolf and R. T. Blikenstaff, J. Org. Chem., 1976, 41, 1254 CrossRef CAS.
  8. P. S. Wharton and D. H. Bohlen, J. Org. Chem., 1961, 26, 3616 CrossRef.
  9. H. L. Holland, J. A. Roas and P. C. Chenchaiah, J. Chem. Soc., Perkin Trans. 1, 1988, 2027 RSC.
  10. J. E. Bridgeman, P. C. Cherry, A. S. Clegg, J. M. Evans, Sir Ewart Jones, A. Kasal, V. Kumar, G. D. Meakins, Y. Morisawa, E. E. Richards and P. D. Woodgate, J. Chem. Soc. (C), 1970, 250 RSC.
  11. Dictionary of Steroids, ed. R. A. Hill, D. N. Kirk, H. L. Makin and G. M. Murphy, Chapman and Hall, London, 1992 Search PubMed.
  12. K. I. H. Williams, Steroids, 1963, 1, 377 CAS.
  13. S. Julia, P. A. Plattner and H. Heusser, Helv. Chim. Acta, 1952, 35, 665 CrossRef CAS.
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