Chirality probing of amino alcohols with lanthanide complexes via induced circular dichroism spectroscopy

(Note: The full text of this document is currently only available in the PDF Version )

Hiroshi Tsukube, Miwa Hosokubo, Masatoshi Wada, Satoshi Shinoda and Hitoshi Tamiaki


Abstract

Achiral lanthanide tris(β-diketonates) selectively formed 1∶1 highly coordinated complexes with amino alcohols and the resulting complexes exhibited characteristic circular dichroism signals depending on the absolute configuration of the bound guests.


References

  1. (a) Y. Kikuchi, K. Kobayashi and Y. Aoyama, J. Am. Chem. Soc., 1992, 114, 1351 CrossRef CAS; (b) T. Morozumi and S. Shinkai, J. Chem. Soc., Chem. Commun., 1994, 1219 RSC; (c) M. Crossley, L. G. Mackay and A. C. Try, J. Chem. Soc., Chem. Commun., 1995, 1925 RSC; (d) H. Tamiaki, N. Matsumoto and H. Tsukube, Tetrahedron Lett., 1997, 38, 4239 CrossRef CAS; (e) T. Mizutani, T. Kurahashi, T. Murakami, N. Matsumi and H. Ogoshi, J. Am. Chem. Soc., 1997, 119, 8991 CrossRef; (f) X. Huang, B. H. Rickman, B. Borhan, N. Berova and K. Nakanishi, J. Am. Chem. Soc., 1998, 120, 6185 CrossRef CAS; (g) E. Yashima, T. Natsushima and Y. Okamoto, J. Am. Chem. Soc., 1997, 119, 6345 CrossRef CAS.
  2. L. A. Laplanche and G. Vanderkooi, J. Chem. Soc., Perkin Trans. 2, 1983, 1585 RSC.
  3. (a) M. Bednarski and S. Danishefsky, J. Am. Chem. Soc., 1983, 105, 3716 CrossRef; (b) M. Calmes, J. Daunis, R. Jacquier and J. Verducci, Tetrahedron, 1987, 43, 2285 CrossRef CAS; (c) F. E. Ziegler and S. B. Sobolov, J. Am. Chem. Soc., 1990, 112, 2749 CrossRef CAS; (d) S. Aime, M. Botta, M. Fasano and E. Terreno, Chem. Soc. Rev., 1998, 27, 19 RSC.
  4. S. Radzki and C. Giannotti, Inorg. Chim. Acta, 1993, 205, 213 CrossRef CAS.
  5. H. Tsukube, S. Shinoda, J. Uenishi, T. Kanatani, H. Itoh, M. Shiode, T. Iwachido and O. Yonemitsu, Inorg. Chem., 1998, 37, 1585 CrossRef CAS.
  6. S. W. Graves, J. A. Fox and B. M. Babior, Biochemistry, 1980, 19, 3630 CrossRef CAS; T. Shibata, T. Takahashi, T. Konishi and K. Soai, Angew. Chem., Int. Ed. Engl., 1997, 36, 2458 CAS; T. Schrader, J. Org. Chem., 1998, 63, 264 CrossRef CAS.
  7. The ionic radii reported for coordination number 6 are shown: R. D. Shannon, Acta Crystallogr., Sect. A, 1976, 32, 751 Search PubMed.
Click here to see how this site uses Cookies. View our privacy policy here.