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The Synthesis of Oxazaborolo-benzoxazaborinine Derivatives of Resorcinarene from (1S,2R)-ephedrine

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Abstract

The oxazaborolo-benzoxazaborinine derivatives (3) of resorcinarene have been synthesized from (1S,2R)-ephedrine. The reaction yields the crown and diamond conformers of the bora derivative of resorcinarene in high diastereomeric excess (de > 97%). The crystallographic structure of the crown conformer of (3) was determined.

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References

  1. P. Timmerman, W. Verboom, and D. N. Reinhoudt: Tetrahedron 52, 2663 (1996).

    Google Scholar 

  2. W. Iwanek, Ch. Wolff, and J. Mattay: Tetrahedron Lett. 36, 8969 (1995); (b) Ch. Schmidt, T. Straub, D. Falŕbu, E.F. Paulus, E. Wegelius, E. Kolehmainen, V. Böhmer, K. Rissanen, and W. Vogt: Eur. J. Org. Chem. 3937 (2000); (c) W. Iwanek: Polish J. Chem. 73, 1777 (1999); (d) P.C.B. Page, H. Heaney, and E.P. Sampler: J. Am. Chem. Soc. 121, 6751 (1999); (e) W. Iwanek: Tetrahedron: Asymmetry 9, 3171 (1998); (f) J. Pfeiffer and V. Schurig: J. Chromatogr. A 840, 145 (1999); (g) M.M. Mocerino, B.W. Skelton, and A.H. White: Org. Lett. 2, 3869 (2000); (h) A.D.M. Curtis: Tetrahedron. Lett. 4295 (1997); (i) B. Botta, G.D. Monache, M.C. De Rosa, C. Seri, E. Benedetti, R. Iacovino, M. Botta, F. Corelli, V. Masignani, A. Tafi, E. Gacs-Baitz, A. Santini, and D. Misiti: J. Org. Chem. 63, 1788 (1997); (j) A. Shivanyuk, Ch. Schmidt, V. Böhmer, E.F. Paulus, O. Lukin, and W. Vogt: J. Am. Chem. Soc. 120, 4319 (1998); (k) G. Arnott, P. Page, Philip, H. Heaney, R. Hunter, and E.P. Sampler: Synlett 3, 412 (2001); (l) H. Konishi, T. Tamura, H. Ohkub, K. Kobayashi, and O. Morikawa: Chem. Lett. 685 (1996); (m) C. Agena, Ch. Wolff, and J. Mattay: Eur. J. Org. Chem., 2977 (2001); (n) W. Iwanek and J. Mattay: Lieb. Anal. 1463 (1995); (o) M.T. El Gihani, H. Heaney, and A.M. Slavin: Tetrahedron Lett. 36, 4905 (1995); (p) R. Arnecke, V. Boehmer, S. Friebe, S. Gebauer, G. Krauss, I. Thondorf, and W. Vogt, Tetrahedron Lett. 36, 6221 (1995); (q) K. Airola, V. Böhmer, E. Paulus, K. Rissanen, Ch. Schmidt, I. Thondorf, and W. Vogt: Tetrahedron 53, 10709 (1997).

    Google Scholar 

  3. Y. Tanaka and Y. Aoyama: Bul: Chem. Soc. Jpn. 63, 3343 (1990); (b) Y. Kikushi, Y. Kato, Y. Tanaka, H. Toi, and Y. Aoyama: J. Am. Chem. Soc. 113, 1349 (1991); (c) Y. Tanaka. Y. Ubukuda, and Y. Aoyama: Chem. Lett. 1905 (1989); (d) K. Kobayashi, Y. Asakawa, Y. Kikushi, H. Toi, and Y. Aoyama: J. Am. Chem. Soc. 115, 2648 (1993); (e) K. Kobayashi, M. Tominaga, Y. Asakawa, and Y. Aoyama Tetrahedron. Lett. 34, 5121 (1993).

    Google Scholar 

  4. W. Iwanek, R. Fröhlich, P. Schwab, and V. Schurig: Chem. Commun., 2516 (2002).

  5. P.D. Woodgate, G.M. Horner, N.P. Maynard, and C.E. Rickard: J. Organometall. Chem. 592, 180 (1999); (b) H.I. Beltram, S.J. Alas, R. Santillan, and N. Farfan: Can. J. Chem. 80, 801 (2002).

    Google Scholar 

  6. L. Abis, E. Dalcanale A. Duvosel, and S. Spera: J. Org. Chem. 53, 5475 (1988).

    Google Scholar 

  7. Z. Otwinowski and W. Minor: Meth. Enzymol. 276, 307 (1997).

    Google Scholar 

  8. R.H. Blessing: Acta Cryst. A51, 33 (1995); (b) R.H. Blessing: J. Appl. Cryst. 30, 421 (1997).

    Google Scholar 

  9. G.M. Sheldrick: Acta Cryst. A46, 467 (1990).

    Google Scholar 

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Correspondence to Waldemar Iwanek.

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Iwanek, W., Fröhlich, R. & Schurig, V. The Synthesis of Oxazaborolo-benzoxazaborinine Derivatives of Resorcinarene from (1S,2R)-ephedrine. Journal of Inclusion Phenomena 49, 75–79 (2004). https://doi.org/10.1023/B:JIPH.0000031116.87700.f3

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  • DOI: https://doi.org/10.1023/B:JIPH.0000031116.87700.f3

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