A stereoselective synthesis of asymmetrically substituted calix[4]arenecarbamates

Tetrahedron Letters

Volumn 47, Issue 44, 2006, Pages 7775-7778

  Boyko, Vyacheslav I ^a   Shivanyuk, Alexander ^a   Pyrozhenko, Volodymyr V ^a   Zubatyuk, Roman I ^b   Shishkin, Oleg V ^b   Kalchenko, Vitaly I ^a  

^a INSTITUTE OF HYDROBIOLOGY   (Ukraine)

^b INSTITUTE FOR SINGLE CRYSTALS   (Ukraine)

Author keywords

Asymmetric synthesis; Calixarenes; Chirality

Indexed keywords

CALIXARENE; CARBAMIC ACID DERIVATIVE; ISOCYANIC ACID DERIVATIVE;

ARTICLE; CHIRALITY; DIASTEREOISOMER; STEREOCHEMISTRY; SUBSTITUTION REACTION; SYNTHESIS;

EID: 33748967953     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.08.095     Document Type: Article

References (34)

1. Gutsche C.D. Calixarenes revisited. In: Stoddart J.F. (Ed). Monographs in Supramolecular Chemistry (1998), Royal Society of Chemistry, Cambridge
2. Asfari Z., Böhmer V., Harrowfield J., and Vicens J. Calixarenes 2001 (2001), Kluwer Academic, Dordrecht
3. Böhmer V. Angew. Chem., Int. Ed. Engl. 34 (1995) 713-745
4. Higler I., Timmerman P., Verboom V., and Reinhoudt D.N. Eur. J. Org. Chem. (1998) 2689-2702
5. Rebek Jr. J. Chem. Commun. (2000) 637-643
6. Rudkevich D.M. Bull. Chem. Soc. Jpn. 75 (2002) 393-413
7. Timmerman P., Vreekamp R.H., Hulst R., Verboom W., Reinhoudt D.N., Rissanen K., Udachin K.A., and Ripmeester J. Chem. Eur. J. 3 (1997) 1823-1832
8. Shivanyuk A., Saadioui M., Thondorf I., Broda F., Rissanen K., Vysotsky M.O., Kolehmainen E., and Böhmer V. Chem. Eur. J. 10 (2004) 2138-2148
9. For a review see:. Vysotsky M., Schmidt C., and Böhmer V. Advances in Supramolecular Chemistry 7 (2000) 139-233
10. Dalla Cort A., Mandolini L., Pasquini C., and Schiaffino L. New J. Chem. 10 (2004) 1198-1199
11. Steyer S., Jeunesse C., Harrowfield J., and Matt D. Dalton Trans. (2005) 1301-1309
12. Gaeta C., De Rosa M., Fruilo M., Soriente A., and Neri P. Tetrahedron: Asymmetry 16 (2005) 2333-2340
13. Kubo Y., Maeda S.Y., Tokita S., and Kubo M. Nature 382 (1996) 522-524
14. Zheng Y.-S., and Zhang C. Org. Lett. 8 (2004) 1189-1192
15. Pappalardo S., Caccamese S., and Giunta L. Tetrahedron Lett. 32 (1991) 7747-7750
16. Ferguson G., Gallagher J.F., Giunta L., Pappalardo S., and Parisi M. J. Org. Chem. 59 (1994) 42-53
17. Ikeda A., Yoshimuira M., Lhotak P., and Shinkai S. J. Chem. Soc., Perkin Trans. 1 (1996) 1945-1950
18. Arnaud-Neu F., Caccamese S., Fuangswasdi S., Pappalardo S., Parisi M.F., Petringa A., and Principato G. J. Org. Chem. 62 (1997) 8041-8048
19. Jin T. Chem. Commun. (1998) 1357-1358
20. Caccamese S., Bottino A., Cunsolo F., Parlato S., and Neti P. Tetrahedron: Asymmetry 11 (2000) 3103-3112
21. Hesek D., Inoue Y., Drew M.G.B., Beer P.D., Hembury G.A., Ishida H., and Aoki F. Org. Lett. 2 (2000) 2237-2240
22. Tairov M.A., Vysotsky M.O., Kalchenko O.I., Pirozhenko V.V., and Kalchenko V.I. J. Chem. Soc., Perkin Trans. 1 (2002) 1405-1411
23. Dieleman C., Steyer S., Jeunesse C., and Matt D. Dalton Trans. (2001) 2508-2517
24. Iwamoto K., Shimizu H., Araki K., and Shinkai S. J. Am. Chem. Soc. 115 (1993) 3997-4006
25. Xu B., Carroll P.J., and Swager T.M. Angew. Chem., Int. Ed. 35 (1996) 2094-2097
26. Cao Y.-D., Luo J., Zheng Q.-Y., Chen M.-X., Wang M.-X., and Huang Z.-T. J. Org. Chem. 69 (2004) 206-208
27. Narumi F., Hattori T., Yamabuki W., Kabuto C., and Kameyama H. Tetrahedron: Asymmetry 16 (2005) 793-800
28. Miao R., Zheng Q.-Y., Chen C.-F., and Huang Z.-T. J. Org. Chem. 70 (2005) 7662-7671
29. 3) δ ppm: 0.99 (s, 9H), 1.01 (s, 9H), 1.29 (s, 18H), 1.68 (d, J = 7.1 Hz, 3H), 3.36 (d, J = 12.9 Hz, 1H), 3.38 (d, J = 13.2 Hz, 1H), 3.39 (d, J = 13.2 Hz, 1H), 3.40 (d, J = 12.9 Hz, 1H), 3.77 (s, 3H), 4.12 (d, J = 13.2 Hz, 1H), 4.17 (d, J = 13.2 Hz, 1H), 4.22 (d, J = 12.9 Hz, 1H), 4.29 (d, J = 12.9 Hz, 1H), 4.48 (d, J = 14.7 Hz, 1H), 4.56 (d, J = 14.7 Hz, 1H), 5.33 (m, 1H), 6.85 (d, J = 2.4 Hz, 2H), 6.88 (d, J = 2.4 Hz, 1H), 6.90 (d, J = 2.4 Hz, 1H), 7.05 (d, J = 2.4 Hz, 1H), 7.07 (d, J = 2.4 Hz, 1H), 7.10 (d, J = 2.4 Hz, 2H), 7.34 (m, 3H), 7.49 (s, 1H), 7.54 (m, 2H), 7.57 (s, 1H), 9.05 (d, J = 8.2 Hz, 1H).
30. Yakovenko A.V., Boyko V.I., Kushnir O.V., Tsymbal I.F., Lipkowski J., Shivanyuk A., and Kalchenko V.I. Org. Lett. 6 (2004) 2769-2772
31. 7: C 68.80, H 6.87, Cl 10.50, N 2.77. Found: C 69.01, H 6.75, Cl 10.42, N 2.86.
32. 1H NMR spectra of the crude products.
33. The yield was calculated for two steps on the basis of the amount of tert-butylcalix[4]arene monomethyl ether used in the synthesis.
34. # = RT ln 4, where 4 is the observed diastereomeric ratio.