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Volumn 63, Issue 20, 1998, Pages 7030-7036

Chiral synthesis via organoboranes. 47. Efficient synthesis of unsymmetrical ketones and enantiomerically pure spiroketals using (±)-isopinocampheyldichloroborane

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EID: 0037884085     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980989w     Document Type: Article
Times cited : (7)

References (74)
  • 1
    • 85034184515 scopus 로고    scopus 로고
    • Present address: Bayer Corp., 8400 Hawthorn Rd., P.O. Box 4913, Kansas City, MO 64120-0013. (b) Present address: Unilever Research U.S. Inc., 45 River Rd., Edgewater, NJ 07020. (c) Present address: Bristol-Myers Squibb Co., Pharmaceutical Group, P.O. Box 4755, Syracuse, NY 13221-4755.
    • (a) Present address: Bayer Corp., 8400 Hawthorn Rd., P.O. Box 4913, Kansas City, MO 64120-0013. (b) Present address: Unilever Research U.S. Inc., 45 River Rd., Edgewater, NJ 07020. (c) Present address: Bristol-Myers Squibb Co., Pharmaceutical Group, P.O. Box 4755, Syracuse, NY 13221-4755.
  • 41
    • 0003463148 scopus 로고
    • Greene, T. W., Wuts, P. G. M., Eds.; John Wiley and Sons: New York
    • (a) Protective Groups in Organic Synthesis, 2nd ed.; Greene, T. W., Wuts, P. G. M., Eds.; John Wiley and Sons: New York, 1991.
    • (1991) Protective Groups in Organic Synthesis, 2nd Ed.
  • 42
    • 0003405159 scopus 로고
    • Georg Thieme Verlag: Stuttgart, New York
    • (b) Kocienski, P. J., Protective Groups; Georg Thieme Verlag: Stuttgart, New York, 1994.
    • (1994) Protective Groups
    • Kocienski, P.J.1
  • 52
    • 85034199525 scopus 로고    scopus 로고
    • note
    • The much faster rate of hydroboration using this method as compared to thexylchloroborane was thought to be advantageous since the protected homoallylic alcohol would remain in contact with the chloroborane for a much shorter time and at a lower temperature, which should minimize side reactions.
  • 57
    • 85034180120 scopus 로고    scopus 로고
    • note
    • Since an excess of MegSiH was not found to have any deleterious effect on the reaction, a moderate excess (1.5 equiv) of it was used to avoid having to measure accurately this low-boiling (bp 7 °C) liquid.
  • 58
    • 85034189039 scopus 로고    scopus 로고
    • note
    • To find the amount of scrambling, the trialkylborane 15 in each case was converted into the unsymmetrical ketone 17, as described in this paper. The amounts of di-ra-hexyl ketone and di-n-octyl ketone formed along with this unsymmetrical ketone 17 gave a direct measure of the amount of scrambling.
  • 62
    • 0001488391 scopus 로고
    • and references therein.
    • Keck, G. J. Am. Chem. Soc. 1993, 115, 8467 and references therein.
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 8467
    • Keck, G.1
  • 69
    • 85034195550 scopus 로고    scopus 로고
    • note
    • 13C NMR since any racemization would have resulted in the formation of diastereomers of 28. Further, the enantiomeric purity of the spiroketal 29 was confirmed by chiral capillary GC in comparison with the racemic spiroketal.
  • 70
    • 0003726028 scopus 로고
    • Wiley-Interscience: New York, A reprinted edition of Vol. 1, Aldrich Chemical Co., Inc., Milwaukee, WI, 1997, is currently available.
    • Brown, H. C.; Kramer, G. W.; Levy, A. B.; Midland, M. M. Organic Synthesis via Boranes; Wiley-Interscience: New York, 1975. A reprinted edition of Vol. 1, Aldrich Chemical Co., Inc., Milwaukee, WI, 1997, is currently available.
    • (1975) Organic Synthesis via Boranes
    • Brown, H.C.1    Kramer, G.W.2    Levy, A.B.3    Midland, M.M.4


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