Utility of a diene–tricarbonyliron complex as mobile chiral auxiliary: iterative use for constructing contiguous chiral centers

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Yoshiji Takemoto, Toshiro Ibuka, Yoshiji Takemoto, Yasutaka Baba, Naoki Yoshikawa, Chuzo Iwata and Tetsuaki Tanaka


Abstract

Three stereogenic centers bearing azide, methoxy, and ethylthio groups, have been constructed stereoselectively using the sole chirality of the Fe(CO)3 group with concurrent 1,2-migration of the Fe(CO)3 group and the obtained product was converted to an anti-aminoalcohol derivative to determine the absolute stereochemistry.


References

  1. P. J. Harrington, Transition Metals in Total Synthesis, John Wiley & Sons, New York, 1990 Search PubMed; J. P. Collman, L. S. Hegedus, J. R. Norton and R. G. Finke, Principles and Applications of Organotransition Metal Chemistry, University Science Books, Mill Valley, CA, 1987 Search PubMed.
  2. W. A. Donaldson, Aldrichim Acta, 1997, 30, 17 Search PubMed; A. J. Pearson, Iron Compounds in Organic Synthesis, Academic Press, London, 1994 Search PubMed; R. Gree, Synthesis, 1989, 341 Search PubMed.
  3. C. Tao, Encyclopedia of Reagents for Organic Synthesis, ed. L. A. Paquette, John Wiley & Sons, London, 1995, vol. 7, p. 5043 Search PubMed.
  4. A. Braun, L. Toupet and J.-P. Lellouche, J. Org. Chem., 1996, 61, 1914 CrossRef CAS; D. M. Gree, J. T. Martelli, R. L. Gree and L. J. Toupet, J. Org. Chem., 1995, 60, 2316 CrossRef CAS; W. A. Donaldson, P. T. Bell, Z. Wang and D. W. Bennett, Tetrahedron Lett., 1994, 35, 5829 CrossRef CAS; C. Quirosa-Guillou and J.-P. Lellouche, J. Org. Chem., 1994, 59, 4693 CrossRef CAS; W. R. Roush and C. K. Wada, Tetrahedron Lett., 1994, 35, 7347 CrossRef CAS.
  5. Y. Takemoto, N. Yoshikawa and C. Iwata, J. Chem. Soc., Chem. Commun., 1995, 631 RSC.
  6. S. Harusawa, R. Yoneda, T. Kurihara, Y. Hamada and T. Shioiri, Tetrahedron Lett., 1984, 25, 427 CrossRef CAS.
  7. E. A. Jares-Erijiman, C. P. Bapat, A. Lithgow-Bertelloni, K. L. Rinehart and R. Sakai, J. Org. Chem., 1989, 54, 366 CrossRef.
  8. Y. Takemoto, Y. Baba, I. Noguchi and C. Iwata, Tetrahedron Lett., 1996, 37, 3345 CrossRef CAS.
  9. H. Takhashi, T. Kawakita, M. Ohno, M. Yoshikawa and S. Kobayashi, Tetrahedron, 1992, 48, 5691 CrossRef CAS.
  10. K. Mori and H. Matsuda, Liebigs Ann. Chem., 1992, 131 Search PubMed.
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