Bulletin of the Korean Chemical Society

  • 제17권6호
  • /
  • Pages.556-558
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  • 1996
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  • 0253-2964(pISSN)
  • /
  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
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A Synthetic Route to a $C_2$-Symmetrical Alkoxyketone

  • 발행 : 1996.06.20
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초록

키워드

참고문헌

  1. Asymmetric Catalysis In Organic Synthesis Noyori, R.
  2. Catalytic Asymmetric Synthesis Ojima, I.(ed.)
  3. Chem. Rev. v.89 Whitesell, J. K.
  4. J. Am. Chem. Soc. v.113 Burk, M. J.
  5. J. Am. Chem. Soc. v.113 Evans, D. A.;Woerpel, K. A.;Hinma, M. M.
  6. J. Am. Chem. Soc.l v.102 Katsuki, T.;Sharpless, K. B.
  7. J. Am. Chem. Soc. v.112 Zhang, W.;Loebach, J. L.;Wilson, S. R.;Jacobsen, E. N
  8. J. Am. Chem. Soc. v.110 Kitamura, M.;Ohkuma, T.;Inoue, S.;Sayo, N.;Kumobayashi, S.;Ohta, T.;Takaya, H.;Noyori, R.
  9. Angew. Chem. Int. Ed. Engl. v.32 Enders, D.;Ducker, B.
  10. J. Am. Chem. Soc. v.109 Fraser, R. R.;Stanciulescu, M.
  11. J. Org. Chem. v.46 Nakazaki, M.;Chikamutsu, H.;Nishino, M.;Murakami, H.
  12. J. Am. Chem. Soc. v.103 Hoye, T. R.;Peck, D. R.;Trumper, P. K.
  13. Synthesis Enders, D.;Gatzweiler, Jegelka, U.
  14. J. Am. Chem. Soc. v.118 During the preparation of this manuscript, catalytic asymmetric epoxidation using a C₂symmetric chiral ketone was published Yang, D.;Yip, Y. C.;Tang, M. W.;Wong, M. K.;Zheng, J. H.;Cheung, K. K.
  15. Angew. Chem. Int. Ed. Engl. v.10 Compound 2 was prepared from L-arabitol according to the following literatue and by further transformations Bestmann, H. J.;Heid, H. A.
  16. We have tried three conditions: PhCHo, p-TsOH in benzene or PhCH(OMe)₂,p-TsOH in CH₂CL₂ or PhCHO, H₂SO₄in DMF.
  17. The ratios were determined by H NMR after oxidation of the liberated alcohol to ketone. The epimers of the ketones were 1 : 1 mixtures.
  18. J. Am. Chem. Soc. v.112 Nakatsuka, M.;Regan, J. A.;Sammakia, T.;Smith, D. B.;Uehling, D. E.;Schreiber, S. L.
  19. NaOMe treatment was not a reproducible procedure in affording 6 in good yields
  20. Aldrichim. Acta. v.23 Griffith, W. P.;Ley, S. V.