Synthesis and Structure of Chiral Cone Calix[4]arenes Functionalized at the Upper Rim with L-Alanine Units

European Journal of Organic Chemistry

Volumn , Issue 5, 1998, Pages 897-905

  Sansone, Francesco ^a   Barboso, Silvia ^a   Casnati, Alessandro ^a   Fabbi, Massimo ^a   Pochini, Andrea ^a   Ugozzoli, Franco ^b   Ungaro, Rocco ^a  

^a UNIVERSITY OF PARMA   (Italy)

^b Ctro Stud Strutturistica D   (Italy)

Author keywords

Amino acids; Calixarenes; Chiral hosts; L Alanine

Indexed keywords

EID: 2742586108     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-0690(199805)1998:5<897::AID-EJOC897>3.0.CO;2-K     Document Type: Article

References (43)

1. Comprehensive Supramolecular Chemislry, Vol. 2, F. Vögtle (ed.), Pergamon Press, 1996.
2. A. P. Davis, Chem. Soc. Rev. 1993, 22, 243-253.
3. J. Jiménez-Barbero, E. Junquera, M. Martin-Pastor, S. Sharma, C. Vicent, S. Penadés, J. Am. Chem. Soc. 1995, 117, 11198-11204.
4. R. Liu, W. C. Still, Tetrahedron Lett. 1993, 34, 2573-2576. - S. S. Yoon, W. C. Still, J. Am. Chem. Soc 1993, 115, 823-824. - S. S. Flack, J. D. Kilburn, Tetrahedron Lett. 1995, 36, 3409-3412. - R P. Bonar-Law, K. M. Sanders, J. Am. Chem. Soc. 1995, 117, 259-271. - S. Kohmoto, D. Fukui, T. Nagashima, K. Kishikawa, M. Yamamoto, K. Yamada, J. Chem. Soc., Chem. Commun. 1996, 1869-1870. - R. Pieters, F. Diederich, J. Chem. Soc., Chem. Commun. 1996, 2255-2256.
5. R. Liu, W. C. Still, Tetrahedron Lett. 1993, 34, 2573-2576. - S. S. Yoon, W. C. Still, J. Am. Chem. Soc 1993, 115, 823-824. - S. S. Flack, J. D. Kilburn, Tetrahedron Lett. 1995, 36, 3409-3412. - R P. Bonar-Law, K. M. Sanders, J. Am. Chem. Soc. 1995, 117, 259-271. - S. Kohmoto, D. Fukui, T. Nagashima, K. Kishikawa, M. Yamamoto, K. Yamada, J. Chem. Soc., Chem. Commun. 1996, 1869-1870. - R. Pieters, F. Diederich, J. Chem. Soc., Chem. Commun. 1996, 2255-2256.
6. R. Liu, W. C. Still, Tetrahedron Lett. 1993, 34, 2573-2576. - S. S. Yoon, W. C. Still, J. Am. Chem. Soc 1993, 115, 823-824. - S. S. Flack, J. D. Kilburn, Tetrahedron Lett. 1995, 36, 3409-3412. - R P. Bonar-Law, K. M. Sanders, J. Am. Chem. Soc. 1995, 117, 259-271. - S. Kohmoto, D. Fukui, T. Nagashima, K. Kishikawa, M. Yamamoto, K. Yamada, J. Chem. Soc., Chem. Commun. 1996, 1869-1870. - R. Pieters, F. Diederich, J. Chem. Soc., Chem. Commun. 1996, 2255-2256.
7. R. Liu, W. C. Still, Tetrahedron Lett. 1993, 34, 2573-2576. - S. S. Yoon, W. C. Still, J. Am. Chem. Soc 1993, 115, 823-824. - S. S. Flack, J. D. Kilburn, Tetrahedron Lett. 1995, 36, 3409-3412. - R P. Bonar-Law, K. M. Sanders, J. Am. Chem. Soc. 1995, 117, 259-271. - S. Kohmoto, D. Fukui, T. Nagashima, K. Kishikawa, M. Yamamoto, K. Yamada, J. Chem. Soc., Chem. Commun. 1996, 1869-1870. - R. Pieters, F. Diederich, J. Chem. Soc., Chem. Commun. 1996, 2255-2256.
8. R. Liu, W. C. Still, Tetrahedron Lett. 1993, 34, 2573-2576. - S. S. Yoon, W. C. Still, J. Am. Chem. Soc 1993, 115, 823-824. - S. S. Flack, J. D. Kilburn, Tetrahedron Lett. 1995, 36, 3409-3412. - R P. Bonar-Law, K. M. Sanders, J. Am. Chem. Soc. 1995, 117, 259-271. - S. Kohmoto, D. Fukui, T. Nagashima, K. Kishikawa, M. Yamamoto, K. Yamada, J. Chem. Soc., Chem. Commun. 1996, 1869-1870. - R. Pieters, F. Diederich, J. Chem. Soc., Chem. Commun. 1996, 2255-2256.
9. R. Liu, W. C. Still, Tetrahedron Lett. 1993, 34, 2573-2576. - S. S. Yoon, W. C. Still, J. Am. Chem. Soc 1993, 115, 823-824. - S. S. Flack, J. D. Kilburn, Tetrahedron Lett. 1995, 36, 3409-3412. - R P. Bonar-Law, K. M. Sanders, J. Am. Chem. Soc. 1995, 117, 259-271. - S. Kohmoto, D. Fukui, T. Nagashima, K. Kishikawa, M. Yamamoto, K. Yamada, J. Chem. Soc., Chem. Commun. 1996, 1869-1870. - R. Pieters, F. Diederich, J. Chem. Soc., Chem. Commun. 1996, 2255-2256.
10. A. Marra, M.-C. Scherrmann, A. Dondoni, A. Casnati, P. Minari, R. Ungaro, Angew. Chem., Int Ed. Engl. 1994, 33, 2479-2481.
11. A. Dondoni, A. Marra, M.-C. Scherrmann, A. Casnati, F. Sansone, R. Ungaro, Chem. Eur. J. 1997, 3, 1774-1782.
12. For recent review articles on calixarenes see: V. Böhmer, Angew. Chem. 1995, 707, 785; Angew. Chem. Int. Ed. Engl. 1995, 34, 713-745. - A. Pochini, R. Ungaro, in Comprehensive Supramolecular Chemistry, Vol. 2, F. Vögtle (ed.), Pergamon Press, 1996, 103-142.
13. For recent review articles on calixarenes see: V. Böhmer, Angew. Chem. 1995, 707, 785; Angew. Chem. Int. Ed. Engl. 1995, 34, 713-745. - A. Pochini, R. Ungaro, in Comprehensive Supramolecular Chemistry, Vol. 2, F. Vögtle (ed.), Pergamon Press, 1996, 103-142.
14. For recent review articles on calixarenes see: V. Böhmer, Angew. Chem. 1995, 707, 785; Angew. Chem. Int. Ed. Engl. 1995, 34, 713-745. - A. Pochini, R. Ungaro, in Comprehensive Supramolecular Chemistry, Vol. 2, F. Vögtle (ed.), Pergamon Press, 1996, 103-142.
15. J. Scheerder, M. Fochi, J. F. J. Engbersen, D. N. Reinhoudt, J. Org. Chem. 1994, 59, 7815-7820. - J. Scheerder, J. F. J. Engbersen, A. Casnati, R. Ungaro, D. N. Reinhoudt, J. Org. Chem. 1995, 60, 6448-6450. - A. Casnati, M. Fochi, P. Minari, A. Pochini, M. Reggiani, R. Ungaro, Gazz. Chim. Ital. 1996, 126, 99-106.
16. J. Scheerder, M. Fochi, J. F. J. Engbersen, D. N. Reinhoudt, J. Org. Chem. 1994, 59, 7815-7820. - J. Scheerder, J. F. J. Engbersen, A. Casnati, R. Ungaro, D. N. Reinhoudt, J. Org. Chem. 1995, 60, 6448-6450. - A. Casnati, M. Fochi, P. Minari, A. Pochini, M. Reggiani, R. Ungaro, Gazz. Chim. Ital. 1996, 126, 99-106.
17. J. Scheerder, M. Fochi, J. F. J. Engbersen, D. N. Reinhoudt, J. Org. Chem. 1994, 59, 7815-7820. - J. Scheerder, J. F. J. Engbersen, A. Casnati, R. Ungaro, D. N. Reinhoudt, J. Org. Chem. 1995, 60, 6448-6450. - A. Casnati, M. Fochi, P. Minari, A. Pochini, M. Reggiani, R. Ungaro, Gazz. Chim. Ital. 1996, 126, 99-106.
18. B. C. Hamann, K. D. Shimisu, J. Rebek jr., Angew. Chem. Int. Ed Engl., 1996, 35, 1326-1329. - O. Mogck, E. F. Paulus, V. Böhmer, I. Thondorf, W. Vogt, J. Chem. Soc., Chem Commun. 1996, 2533-2534.
19. B. C. Hamann, K. D. Shimisu, J. Rebek jr., Angew. Chem. Int. Ed Engl., 1996, 35, 1326-1329. - O. Mogck, E. F. Paulus, V. Böhmer, I. Thondorf, W. Vogt, J. Chem. Soc., Chem Commun. 1996, 2533-2534.
20. Molecular Recognition. Chemical and Biochemical Problems Roberts S. M. Ed., RSC, Special Publication no. 78, 1990.
21. W. H. Pirkle, T. C. Pochapsky, Chem Rev. 1989, 89, 347-362. - J. C. Welch, J. Chromatogr. A 1994, 666, 3-26.
22. W. H. Pirkle, T. C. Pochapsky, Chem Rev. 1989, 89, 347-362. - J. C. Welch, J. Chromatogr. A 1994, 666, 3-26.
23. E. L. Eliel, S. H. Wilen, Stereochemistry of Organic Compounds cpt 12, J. Wiley & Sons, New York, 1994.
24. T. Nagasaki, Y. Tajiri, S. Shinkai, Rec. Trav. Chim. Pays-Bas 1993, 112, 407-411. - M. S. Peña, Y. Zhang, S. Thibodeaux, M. L. McLaughlin, A. M. de la Peña, I. M. Warner, Tetrahedron Lett. 1996, 37, 5841-5844. - B. C. Gibb, A. R. Mezo, A. S. Causton, J. R. Fraser, F. C. S. Tsai, J. C. Sherman, Tetrahedron 1995, 51, 8719-8732. - Y. Murakami, O. Hayashida, Y. Nagai, J. Am. Chem. Soc. 1994, 116, 2611-2612.
25. T. Nagasaki, Y. Tajiri, S. Shinkai, Rec. Trav. Chim. Pays-Bas 1993, 112, 407-411. - M. S. Peña, Y. Zhang, S. Thibodeaux, M. L. McLaughlin, A. M. de la Peña, I. M. Warner, Tetrahedron Lett. 1996, 37, 5841-5844. - B. C. Gibb, A. R. Mezo, A. S. Causton, J. R. Fraser, F. C. S. Tsai, J. C. Sherman, Tetrahedron 1995, 51, 8719-8732. - Y. Murakami, O. Hayashida, Y. Nagai, J. Am. Chem. Soc. 1994, 116, 2611-2612.
26. T. Nagasaki, Y. Tajiri, S. Shinkai, Rec. Trav. Chim. Pays-Bas 1993, 112, 407-411. - M. S. Peña, Y. Zhang, S. Thibodeaux, M. L. McLaughlin, A. M. de la Peña, I. M. Warner, Tetrahedron Lett. 1996, 37, 5841-5844. - B. C. Gibb, A. R. Mezo, A. S. Causton, J. R. Fraser, F. C. S. Tsai, J. C. Sherman, Tetrahedron 1995, 51, 8719-8732. - Y. Murakami, O. Hayashida, Y. Nagai, J. Am. Chem. Soc. 1994, 116, 2611-2612.
27. T. Nagasaki, Y. Tajiri, S. Shinkai, Rec. Trav. Chim. Pays-Bas 1993, 112, 407-411. - M. S. Peña, Y. Zhang, S. Thibodeaux, M. L. McLaughlin, A. M. de la Peña, I. M. Warner, Tetrahedron Lett. 1996, 37, 5841-5844. - B. C. Gibb, A. R. Mezo, A. S. Causton, J. R. Fraser, F. C. S. Tsai, J. C. Sherman, Tetrahedron 1995, 51, 8719-8732. - Y. Murakami, O. Hayashida, Y. Nagai, J. Am. Chem. Soc. 1994, 116, 2611-2612.
28. A. Casnati, M. Fabbi, N. Pelizzi, A. Pochini, F. Sansone, R. Ungaro, E. Di Modugno, G. Tarzia, Bioorg. Med. Chem. Lett 1996, 6, 2699-2704.
29. S. Chen, J. Xu, Tetrahedron Lett. 1992, 33, 647-650.
30. M. Bodansky, A. Bodansky, The Practice of Peptide Synthesis, Springer-Verlag Ed. New York, 1984.
31. A. Arduini, M. Fabbi, M. Mantovani, L. Mirone, A. Pochini, A. Secchi, R. Ungaro, J. Org. Chem. 1995, 60, 1454-1457.
32. O. Struck, W. Verboom, W. J. J. Smeets, A. L. Spek, D. N. Reinhoudt, J. Chem. Soc., Perkin Trans. 2 1997, 223-227.
33. M Perrin, D. Oehler, in Calixarenes. A Versatile Class of Macrocyclic Compounds, J. Vicens, V. Böhmer Eds., Kluwer Academic Publishers, Dordrecht, The Netherlands, 1991, 65-85.
34. F. Ugozzoli, G. D. Andreetti, J. Incl. Phen. and Mol. Rec. in Chem. 1992, 13, 337-348.
35. A. Arduini, A. Casnati, Macrocycle Synthesis A Practical Approach, David Parker Ed., Oxford, 1996, 145-173.
36. V. Böhmer, K. Jung, M. Schön, A. Wolff, J. Org. Chem. 1992, 57, 790-792. - Gutsche, C. D.; See, K. A. J. Org. Chem. 1992, 57, 4527-4539.
37. V. Böhmer, K. Jung, M. Schön, A. Wolff, J. Org. Chem. 1992, 57, 790-792. - Gutsche, C. D.; See, K. A. J. Org. Chem. 1992, 57, 4527-4539.
38. M. S. Lehmann, F. K. Larsen, Acta Crystallogr. 1974, sect A, 580-584.
39. Sheldrick, G. SHELX86. Program for Crystal Structure Solutions, University of Göttingen, Germany, 1986.
40. Sheldrick, G. SHELX76 Program for Crystal Structure Determinations, University of Cambridge, England, 1976.
41. D. T. Cromer, J. J. Waber, in International Tables for X-Ray Crystallography, J. A. Ibers and W. C. Hamilton (eds.), 1974, Vol IV, The Kynoch Press, Birmingham, England, Table 2.2.B.
42. D. T Cromer, J. A. Ibers, in international Tables for X-Ray Crystallography, J. A. Ibers and W. C. Hamilton (eds.), 1974, Vol IV, The Kynoch Press, Birmingham, England, Table 2.3.1.
43. M. Nardelli, PARST, Comput & Chem 1983, 7, 95-102.