Bulletin of the Korean Chemical Society

  • 제4권1호
  • /
  • Pages.14-17
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  • 1983
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  • 0253-2964(pISSN)
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  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
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Effect of Trialkylborane on the Stereochemistry of Ketone Reduction with Lithium Borohydride

  • 발행 : 1983.02.20
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초록

The effects of trialkylborane on the stereochemistry of ketone reduction with lithium borohydride were studied for the four representative ketones, namely 4-t-butylcyclohexanone, 2-methylcyclohexanone, norcamphor, and camphor. The presence of trialkylborane increased the yields of the less stable alcohols. For example, in the presence of tri-s-butylborane, 42 % yield of cis-4-t-butylcyclohexanol was observed whereas only 8 % yield with lithium borohydride alone in the reduction of 4-t-butylcyclohexanone. The in situ formation of lithium trialkylborohydride, by the hydride transfer from lithium trialkoxyborohydride to trialkylborane, was demonstrated as a possible mechanism for the catalytic effect of trialkylborane.

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참고문헌

  1. J. Amer. Chem. Soc. v.78 W. G. Dauben;G. J. Fonken;D. S. Noyce
  2. Tetrahedron v.35 H. C. Brown;S. Krishnamurthy
  3. J. Amer. Chem. Soc. v.92 H. C. Brown;W. C. Dickson
  4. J. Amer. Chem. Soc. v.93 E. J. Corey;S. M. Albonico;U. Koelliker;T. K. Schaaf;R. K. Varma
  5. J. Amer. Chem. Soc. v.89 H. C. Brown;C. D. Pfaffenberger
  6. J. Amer. Chem. Soc. v.98 S. Krishnamurthy;H. C. Brown
  7. J. Amer. Chem. Soc. v.94 H. C. Brown;S. Krishnamurthy
  8. J. Korean Chem. Soc. v.21 N. M. Yoon;J. S. Cha
  9. J. Amer. Chem. Soc. v.101 C. A. Brown;J. L. Hubbard
  10. N. M. Yoon;J. S. Cha;I. H. Oh
  11. J. Amer. Chem. Soc. v.78 W. G. Dauben;E. J. Blanz;R. A. Micheli
  12. J. Amer. Chem. Soc. v.84 H. Haubenstock;E. L. Eliel
  13. J. Org. Chem. v.27 H. O. House;H. Babid;R. B. Toothill;A. W. Noltes
  14. J. Org. Chem. v.28 H. O. House;H. C. Muller;C. G. Pitt;P. P. Wickham
  15. J. Org. Chem. v.30 J. C. Richer
  16. Modern Synthetic Reactions H. O. House
  17. Asymmetric Organic Reactions J. D. Morrison;M. S. Mosher
  18. Chem. Rev. v.521 E. C. Ashby;J. T. Laemmle

피인용 문헌

  1. Thirty Six Years of Research on the Selective Reduction and Hydroboration vol.32, pp.6, 1983, https://doi.org/10.5012/bkcs.2011.32.6.1808