Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Selective Reduction of Carbonyl Compounds with Al-Alkoxydiisobutylalanes

  • Published : 1998.02.20
Download PDF
⟨ Previous Next ⟩

Abstract

Reaction of carbonyl compounds with Al-alkoxydiisobutylalane (DIBAOR, R=H, Et, i-Pr, t-Bu) has been investigated in detail so as to establish their usefulness as selective reducing agents in organic synthesis. The reagents appear to be extremely mild and can reduce only aldehydes and ketones effectively under mild conditions. All the other common organic functional groups are not affected by these reagents. The reagents can also reduce α,β-unsaturated aldehydes and ketones to the corresponding allylic alcohols without any detectable 1,4-reduction. Furthermore, the reagents show a highly chemoselective discrimination between aldehyde and ketone, between aldehydes, and between ketones. Even more remarkable is the stereoselective reduction of cyclic ketones to the thermodynamically more stable alcohol epimers.

Keywords

References

  1. Bull. Korean Chem. Soc. v.16 Cha, J. S.;Kown, O. O.;Kwon, S. Y.
  2. Synlett. Cha, J. S.;Kwon, O. O.;Kwon, S. Y.;Kim, J. M.;Seo, W. W.;Chang, S. W.
  3. Bull. Korean Chem. Soc. v.15 Cha, J. S.;Kim, E. J.;Kwon, O. O.;Kim, J. M.
  4. Synlett Cha, J. S.;Kim, E. J.;Kwon, O. O.;Kim, J. M.
  5. Bull. Korean Chem. Soc. v.17 Cha, J. S.;Kim, E. J.;Kwon, O. O.;Kim, J. M.
  6. Asymmetric Synthesis v.2 Morrison, J. D.
  7. Bull. Korean Chem. Soc. v.17 Cha, J. S.;Kwon, O. O.;Kwon, S. Y.;Kim, J. M.;Seo, W. W.;Chang, S. W.
  8. Org. Prep. Proced. Int. v.28 Cha, J. S.;Kwon, O. O.;Kwon, S. Y.
  9. J. Org. Chem. v.62 Cha, J. S.;Kwon, O. O.
  10. Modern Synthetic Reactions(2nd Ed.) House, H. O.;Benjamin, W. A.
  11. Hard and Soft Acids and Bases Principles in Organic Chemistry Ho, T.-L.
  12. J. Chem. Soc. Chem. Commun. Wilson, K. E.;Seidner, R. T.;Masamune, S.
  13. J. Org. Chem. v.35 Johnson, M. R.;Rickborn, B.
  14. J. Org. Chem. v.40 Krishnamurthy, S.;Brown, H. C.
  15. J. Org. Chem. v.42 Idem
  16. J. Org. Chem. v.47 Kim, S.;Moon, Y. C.;Ahn, K. H.
  17. J. Org. Chem. v.40 Ganem, B.
  18. J. Org. Chem. v.41 Ganem, B.;Fortunato, J. M.
  19. J. Org. Chem. v.44 Mordenti, L.;Brunet, J. J.;Caubere, I.
  20. J. Am. Chem. Soc. v.71 Chaikin, S. W.;Brown, W. G.
  21. J. Chem. Soc. v.47 Cain, M. E.
  22. J. Org. Chem. v.34 Brown, H. C.;Hess, H. M.
  23. J. Org. Chem. v.42 Semmelhack, M. F.;Stauffer, R. D.;Yamashta, A.
  24. J. Am. Chem. Soc. v.94 Gemal, A. L.;Luche, T. L.
  25. J. Org. Chem. v.40 Hutchins, R. O.;Kandasamy, D.
  26. J. Am. Chem. Soc. v.94 Corey, E. J.;Becker, K. B.;Varma, R. K.
  27. J. Org. Chem. v.49 Brown, H. C.;Mathew, C. P.;Pyun, C.;Yoon, N. M.
  28. Tetrahedron Lett. v.25 Sande, A. R.;Jagadale, M. H.;Mane, R. B.;Salunkhe, M. M.
  29. Bull. Korean. Chem. Soc. v.17 Cha, J. S.;Kwon, O. O.;Kim, J. M.
  30. Org. Prep. Proced. Int. v.27 Cha, J. S.;Kim, E. J.;Kwon, O. O.;Kwon, S. Y.;Seo, W. W.;Chang, S. W.
  31. Bull. Korean Chem. Soc. v.16 Cha, J. S.;Kim, E. J.;Kwon, O. O.;Kim, J. M.
  32. J. Am. Chem. Soc. v.95 Hutchins, R. O.;Kandasamy, D.
  33. J. Chem. Soc. Chem. Commun. v.95 Gribble, G. W.;Ferguson, D. C.
  34. Aust. J. Chem. v.28 Sell, C. S.
  35. Tetrahedron Lett. Maki, Y.;Kikuchi, K.;Sugiyama, H.;Seto, S.
  36. J. Org. Chem. v.42 Posner, G. H.;Runquist, A. W.;Chadelaine, M.
  37. J. Org. Chem. v.42 Brown, H. C.;Kulkarni, S. V.
  38. J. Korean Chemm. Soc. v.22 Yoon, N. M.;Cha, J. S.
  39. J. Org. Chem. v.43 Fung, N. Y. M.;demayo, P.;Schauble, J. H.;Weedorn, A. C.
  40. J. Org. chem. v.43 Risbood, P. A.;Ruthoven, D. M.
  41. J. Org. Chem. v.40 Risbood, P. A.;Ruthoven, D. M.
  42. J. Org. Chem. v.45 Sorrell, T. N.;Pearlman, P. S.
  43. J. Org. Chem. v.46 Fleet, G. W. J.;Harding, P. J.
  44. J. Org. Chem. v.46 Krishnamurthy, S.
  45. Tetrahedron Lett. Yoon, N. M.;Park, G. B.;Gyoung, Y. S.
  46. Tetrahedron Lett. Ki, S.;Kang, H. J.;Yang, S.
  47. Bull. Korean Chem. Soc. v.9 Kim, S.;Yang, S.
  48. Synth. Commun. v.18 Ward, D. E.;Rhee C. K.
  49. Tetrahedron Lett. v.29 Ward, D. E.;Rhee, C. K.;Zoghaib, W. M.
  50. Tetrahedron Lett. v.29 Maruoka, K.;Araki, Y.;Yamamoto, H.
  51. Tetrahedron Lett. v.31 Ranu, B. C.;Chakraborty, R.
  52. J. Org. Chem. v.55 Sarkas, C. C.;Das, A. R.;Ranu, B. C.
  53. Synth. Commun. v.21 Firouzabadi, H.;Tamami, B.;Goudarzian, N.
  54. J. Am. Chem. Soc. v.94 Brown, H. C.;Krishnamurthy, S.
  55. Aldrichim. Acta. v.7 Krishna-murthy, S.
  56. J. Am. Chem. Soc. v.98 Krishna-murthy, S.;Brown, H. C.
  57. J. Orgamomet. Chem. v.156 Brown, C. A.;Krishnamurthy, S.
  58. Tetrahedron v.35 Brown, H. C.;Krishnamurthy, S.
  59. J. Org. Chem. v.49 Brown, H. C.;Cha, J. S.;Nazer, B.
  60. J. Org. Chem. v.51 Yoon, N. M.;Kim, K. E.;Kang, J.
  61. Tetrahedron Lett. v.29 Cha, J. S.;Yoon, M. S.;Kim, Y. S.;Lee, K. W.
  62. J. Am. Chem. Soc. v.82 Eliel, E. L.;Rerick, M.
  63. Orgnaic Synthesis v.5 Eliel, E. L.;Martin, R. L.;Nasipuri, D.
  64. Can. J. Chem. v.43 Abramovitch, R. A.;Marsh, W. C.;Saha, J. G.
  65. J. Orgamomet. Chem. v.198 Mestroni, G.;Zassinovitch, G.;Camus, A.;Martinelli, F.
  66. J. Organmet. Chem. v.255 Toros, S.;Kollar, L.;Heil, B.;Marko, L.
  67. J. Mol. Cartal v.22 Spogliarich, R.;Mestroni, G.;Graziani, M.
  68. Tetrahedron Lett. v.26 Maruoka, K.;Sakurai, M.;Yamoto, H.
  69. Synth. Commun. v.23 Sarka, A.;Rao, B. R.;Ram, B.
  70. J. Org. Chem. v.59 Fiser, G. B.;Fuller, J. C.;Harrison, J.;Alvarez, S. G.;Burkhardt, E. R.;Goralski, C. T.;Singaram, B.
  71. Tetrahedron Lett. v.36 Fort, Y.
  72. J. Org. Chem. v.35 Ashby, E. C.;Yu, S. H.
  73. J. Org. Chem. v.38 Heinsohn, G. E.;Ashby, E. C.
  74. Synthesis Winterfeldt, E.
  75. J. Org. Chem. v.28 A similar time dependence was reported by Haubenstock and Davidson as observed in the reduction of excess 3,3,5-trimethycyclohexanone with triisobutylaluminum (TIBA) Haubenstock;Davidson
  76. Organic Synthesis via Boranes Brown, H. C.;Kramer, G. W.;Levy, A. B.;Midland, M. M.