Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Asymmetric Reduction of Prochiral Ketones with Potassium 9-O-isopinocampheyloxy-9 boratabicyclo[3.3.1]nonane$^+$

  • Park, Won-Suh (Department of Chemistry, Purdue University, West Lafayette) ;
  • Cho, Byung-Tae (Department of Chemistry, Purdue University, West Lafayette) ;
  • Cha, Jin-Soon (Department of Chemistry, Purdue University, West Lafayette)
  • Published : 1987.06.20
Download PDF
⟨ Previous Next ⟩

Abstract

Asymmetric reduction of a series of aliphatic ketones and representative other classes of ketones with potassium 9-O-isopinocampheyloxy-9-boratabicyclo[3.3.1]non ane (K 9-O-Ipc-9-BBNH) was studied. All the ketones examined were reduced smoothly to the corresponding alcohols in THF at -$78^{\circ}C$. Thus, the reduction of 2-butanone, 3-methyl-2-butanone, 3,3-dimethyl-2-butanone, 2-octanone, and 4-phenyl-2-butanone provides 51% ee, 61% ee, 44% ee, 35% ee, and 33% ee of optical inductions, respectively. The reduction of other classes of ketones gave 52% ee for 2,2-dimethylcyclopentanone, 47% ee for acetophenone, 23% ee for 3-acetylpyridine, 50% ee for methyl benzoylformate, 4.8% ee for 2-chloroacetophenone, 30% ee for trans-4-phenyl-3-butene-2-one, and 2% ee for 4-phenyl-3-butyn-2-one. Thus, the reagent was found to be most useful in the asymmetric reduction of acyclic and cyclic aliphatic series of ketones.

Keywords

References

  1. Asymmetric Organic Reaction Morrison, J.D.;Mosher, H.S.
  2. Synthesis Valentine, D., Jr.;Scott, J.W.
  3. Top. Stereochem. v.10 Kagan, H.B.;Fiaud, J.C.
  4. Tetrahedron v.35 ApSimon, J.W.;Seguin, R.P.
  5. v.2 Midland, M.M.
  6. Asymmetric Synthesis v.2 Grandbois, E.R.;Howard, S.I.;Morrison, J.D.;Morrison, J.D.(ed.)
  7. Top. Stereochem. v.14 Haubenstock, H.
  8. Tetrahedron v.42 ApSimon, J.W.;Lee Collier, T.
  9. J. Org. Chem. v.51 Brown, H.C.;Park, W.S.;Cho, B.T.
  10. J. Org. Chem. v.50 Chandrasekharan, J.;Ramachandran, P.V.;Brown, H.C.
  11. Am. Chem. Soc. v.106 Noyori, R.;Tomino, I.;Tanimoto, Y.;Nishizawa, M.J.
  12. J. Chem. Soc. Perkin Trans. I Itsuno, S.;Nakano, M.;Miyazaki, K.;Masuda, H.;Ito, K.
  13. J. Org. Chem. v.50 Brown, H.C.;Pai, G.G.
  14. Chem. Lett. Soai, K.;Yamanoi, T.;Oyamada, H.
  15. J. Chem. Soc. Chem. Commun. Yamamoto, K.;Fukushima, H.;Nakazaki, M.
  16. J. Org. Chem. v.47 Midland, M.M.;Kazubski, A.
  17. J. Org. Chem. v.51 Brown, H.C.;Chandrasekharan, J.;Ramachandran, P.V.
  18. J. Am. Chem. Soc. v.108 Keinan, E.;Hafeli, E.K.;Seth, K.K.;lamed, R.
  19. J. Am. Chem. Soc. v.108 Imai, T.;Tamura, T.;Yamamura, A.;Sato, T.;Wollman, T.A.;Kennedy, R.M.;Masamune, S.
  20. J. Org. Chem. v.51 Brown, H.C.;Park, W.S.;Cho, B.T.
  21. J. Org. Chem. v.42 Krishnamurthy, S.;Vogel, F.;Brown, H.C.
  22. J. Am. Chem. Soc. v.95 Dale, J.A.;Mosher, H.S.
  23. J. Org. Chem. v.33 Westley, J.W.;Halpern, B.
  24. J. Org. Chem. v.51 Brown, H.C.;Cho, B.T.;Park, W.S.
  25. Organic Syntheses via Boranes Brown, H.C.
  26. J. Org. Chem. v.34 Dale, J.A.;Dull, D.A.;Mosher, H.S.
  27. Chem. Lett. Kawasaki, M.;Suzuki, Y.;Terashima, S.
  28. J. Org. Chem. v.30 Berti, G.;Bottari, F.;Ferrorini, P.L.;Moccia, B.J.