Inherently chiral derivatives of calix[5]crowns

Tetrahedron Letters

Volumn 37, Issue 9, 1996, Pages 1497-1500

  Arnecke, Ralf ^a   Böhmer, Volker ^a   Ferguson, George ^b   Pappalardo, Sebastiano ^c  

^a JOHANNES GUTENBERG UNIVERSITY   (Germany)

^b UNIVERSITY OF GUELPH   (Canada)

^c UNIVERSITY OF CATANIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0343113391     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00048-2     Document Type: Article

References (20)

1. For a recent review on calixarenes see: Böhmer, V. Angew. Chem. 1995, 107, 785-818; Angew. Chem. Int. Ed. Engl. 1995, 34, 713-745.
2. For a recent review on calixarenes see: Böhmer, V. Angew. Chem. 1995, 107, 785-818; Angew. Chem. Int. Ed. Engl. 1995, 34, 713-745.
3. For very recent examples see: Arduini, A.; Pochini, A.; Secchi, A.; Ungaro, R. J. Chem. Soc., Chem. Commun. 1995, 879-880; Timmerman, P.; Nierop, K. G. A.; Prinks, E. A.; Verboom, W.; van Veggel, F. C. J. M.; van Hoorn, W. P.; Reinhoudt, D. N. Chem. Eur. J. 1995, 1, 132-143.
4. For very recent examples see: Arduini, A.; Pochini, A.; Secchi, A.; Ungaro, R. J. Chem. Soc., Chem. Commun. 1995, 879-880; Timmerman, P.; Nierop, K. G. A.; Prinks, E. A.; Verboom, W.; van Veggel, F. C. J. M.; van Hoorn, W. P.; Reinhoudt, D. N. Chem. Eur. J. 1995, 1, 132-143.
5. For a review on inherently chiral calixarenes see: Böhmer, V.; Kraft, D.; Tabatabai, M. J. Incl. Phenom. Mol. Recogn. 1994, 19, 17-39.
6. Ferguson G.; Gallagher, J. F.; Giunta, L.; Neri, P.; Pappalardo, S.; Parisi, M. J. Org. Chem. 1994, 59, 42-53. Pappalardo, S.; Parisi, M. F. Tetrahedron Lett., preceding paper.
7. Ferguson G.; Gallagher, J. F.; Giunta, L.; Neri, P.; Pappalardo, S.; Parisi, M. J. Org. Chem. 1994, 59, 42-53. Pappalardo, S.; Parisi, M. F. Tetrahedron Lett., preceding paper.
8. One type of residue is sufficient when conformations different from cone are fixed. For a survey see: Böhmer, V.; Kraft, D.; Vogt, W. Supramol. Chem. 1994, 3, 299-301.
9. 5-symmetry see: Tabatabai, M.; Böhmer, V.; Vogt, W. Supramol. Chem. 1994, 4, 147-152.
10. Kraft, D.; Arnecke, R.; Böhmer, V.; Vogt, W. Tetrahedron 1993, 49, 6019-6024.
11. 2-ArH).
12. Jaime, C.; de Mendoza, J.; Prados, P.; Nieto, P. M.; Sanchez, C. J. Org. Chem. 1991, 56, 3372-3376; Stewart, D. R.; Krawiec, M.; Kashyap, R. P.; Watson, W. H.; Gutsche, C. D. J. Am. Chem. Soc. 1995, 117, 586-601.
13. Jaime, C.; de Mendoza, J.; Prados, P.; Nieto, P. M.; Sanchez, C. J. Org. Chem. 1991, 56, 3372-3376; Stewart, D. R.; Krawiec, M.; Kashyap, R. P.; Watson, W. H.; Gutsche, C. D. J. Am. Chem. Soc. 1995, 117, 586-601.
14. Pappalardo, S.; Ferguson, G. J. Org. Chem., in the press.
15. +).
16. Assuming the O-picolyl residue in 1-position, 2,3-, 2,4-, 2,5-and 3,4-mono crowns are possible, from which the latter two are achiral.
17. 2) = 0.125. The analysis was complicated by disorder of the pendant O-picolyl and crown-ether moieties as well as the tert-butyl methyl groups; this was allowed for in the refinements. There is an acetonitrile molecule (with unit occupancy) enclathrated within the calix[5]arene cup and another (with occupancy 0.6) in what would have been a void in the crystal lattice between calix[5]arene molecules.
18. Sheldrick, G. M. SHELXS86, Program for the solution of crystal structures, Univ. of Göttingen, Germany, 1986.
19. Gabe, E.J.; Le Page, Y.; Charland, J-P.; Lee, F. L.; White, P. S. J. Appl. Cryst. 1989, 22, 384-389.
20. Sheldrick, G. M. SHELXS93, Program for the refinement of crystal structures, Univ. of Göttingen, Germany, 1993.