Self-assembly of (P)-heterohelicenediol into a four-leaf clover motif

Abstract

(P)-2,13-Bis(hydroxymethyl)heterohelicenediol [(P)-1] self-assembles through a right-handed helical network of hydrogen bonds to form a four-leaf clover motif; a full turn of the helix comprises four chiral subunits which associate in a left-handed helical manner with a 4₃ screw axis.

References

1. J.-M. Lehn, Angew. Chem., Int. Ed. Engl., 1990, 29, 1304.
2. G. R. Desiraju, Angew. Chem., Int. Ed. Engl., 1995, 34, 2311.
3. C. Piguet, J.-C. Bünzli, G. Bernardinelli, G. Hopfgartner, S. Petoud and O. Schaad, J. Am. Chem. Soc., 1996, 118, 6681.
4. D. B. Amabilino and J. F. Soddart, Chem. Ber., 1995, 95, 2725.
5. M. R. Ghadiri, J. R. Granja and L. K. Buehler, Nature, 1994, 369, 301.
6. J. C. MacDonald and G. M. Whitesides, Chem. Rev., 1994, 94, 2383.
7. M. M. Conn and J. Rebeck, Jr., Chem. Ber., 1997, 97, 1647.
8. M. Fugita, D. Oguro, M. Miyazawa, H. Oka, K. Yamaguchi and K. Ogura, Nature, 1995, 378, 469.
9. J. Manna, J. C. Kuel, J. A. Whiteford, P. J. Stang, D. C. Muddiman, S. A. Hofstadler and R. D. Smith, J. Am. Chem. Soc., 1997, 119, 11 611.
10. D. M. Bassani, J.-M. Lehn, G. Baum and D. Fenske, Angew. Chem., Int. Ed. Engl., 1997, 36, 1845.
11. P. N. W. Baxter, H. Sleiman, J.-M. Lehn and K. Rissanen, Angew. Chem., Int. Ed. Engl., 1997, 36, 1297.
12. Y. Hamuro, S. J. Geib and A. D. Hamilton, J. Am. Chem. Soc., 1997, 119, 10 587.
13. A. Williams, Chem. Eur. J., 1997, 3, 15.
14. C. Piguet, G. Bernardinelli and G. Hopfgartner, Chem. Rev., 1997, 97, 2005.
15. K. Tanaka, H. Osuga, H. Suzuki, Y. Shogase and Y. Kitahara, J. Chem. Soc., Perkin Trans. 1, 1998, 935.
16. K. Tanaka, Y. Shogase, H. Osuga, H. Suzuki, W. Nakanishi, N. Nakamura and Y. Kawai, J. Chem. Soc., Chem. Commun., 1995, 1873.