Asymmetric environments in encapsulation complexes

Journal of the American Chemical Society

Volumn 125, Issue 20, 2003, Pages 6239-6243

  Scarso, Alessandro ^a   Shivanyuk, Alexander ^a   Hayashida, Osamu ^a   Rebek Jr , Julius ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COMPLEXES;

CARBOXYLIC ACIDS; ENCAPSULATION; MOLECULES;

COMPLEXATION;

BUTYRIC ACID DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; MANDELIC ACID;

ARTICLE; CHIRALITY; COMPLEX FORMATION; DIASTEREOISOMER; ENANTIOSELECTIVITY; MICROENCAPSULATION; MOLECULAR INTERACTION;

BUTYRIC ACIDS; CHEMISTRY, ORGANIC; CYCLOPROPANES; EPOXY COMPOUNDS; MAGNETIC RESONANCE SPECTROSCOPY; MANDELIC ACIDS; STEREOISOMERISM; SUBSTRATE SPECIFICITY; THERMODYNAMICS; XYLENES;

EID: 0037613294     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja029574p     Document Type: Article

References (37)

1. (a) Canceill, J.; Lacombe, L.; Collet, A. J. Am. Chem. Soc. 1985, 107, 6993-6996.
2. (b) Yoon, J.; Cram, D. J. J. Am. Chem. Soc. 1997, 119, 11796-11806.
3. (c) Judice, J. K.; Cram, D. J. J. Am. Chem. Soc. 1991, 113, 2790-2791.
4. (a) Rivera, J. M.; Martin. T.; Rebek, J., Jr. J. Am. Chem. Soc. 2001, 123, 5213-5220. Tokunaga, J.; Rebek, J., Jr. J. Am. Chem. Soc. 1998, 120, 66-69.
5. (a) Rivera, J. M.; Martin. T.; Rebek, J., Jr. J. Am. Chem. Soc. 2001, 123, 5213-5220. Tokunaga, J.; Rebek, J., Jr. J. Am. Chem. Soc. 1998, 120, 66-69.
6. (b) Castellano, R. K.; Nuckolls, C.; Rebek, J., Jr. J. Am. Chem. Soc. 1999, 121, 11156-11163.
7. (c) Castellano, R. K.; Kim, B. H; Rebek, J., Jr. J. Am. Chem. Soc. 1997, 119, 12671-12672.
8. (d) Nuckolls, C.; Hof, F.; Martin, T.; Rebek, J., Jr. J. Am. Chem. Soc. 1999, 121, 10281.
9. (e) Böhmer, V.; Vysotsky, M. O. Aust. J. Chem. 2001, 54, 671.
10. (f) Sherman, J. C. Tetrahedron 1995, 51, 3395.
11. (g) Hof, F.; Craig, S. L.; Nuckolls, C.; Rebek, J., Jr. Angew. Chem., Int. Ed. 2002, 41, 1488.
12. (a) Lee, S. B.; Hong, J. J. Tetrahedron Lett. 1996, 37, 8501.
13. (b) Corbellini, F.; Fiammengo, R.; Timmerman, P.; Crego-Calama, M.; Versluis, K.; Heck, A. J. R.; Luyten, I.; Reinhoudt, D. N. J. Am. Chem. Soc. 2002, 124, 6569.
14. (a) Fujita, M.; Umemoto, K.; Yoshizawa, M.; Fujita, N.; Kusukawa, T.; Biradha, K. Chem. Commun. 2001, 509-518.
15. (b) Hirakoa, S.; Fujita, M. J. Am. Chem. Soc. 1999, 121, 10239-10240.
16. (c) Kusukawa, T.; Fujita, M. J. Am. Chem. Soc. 2002, 124, 13576-13582.
17. Caulder, D. L.; Raymond, K. N. Acc. Chem. Res. 1999, 32, 975-892.
18. (a) Heinz, T.; Rudkevich, D.; Rebek, J., Jr. Nature 1998, 394, 764-766.
19. (b) Ebbing, M. K.; Villa, M.-J.; Malpuesta, J.-M.; Prados, P.; de Mendoza, J. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 4962-4966.
20. (c) Shivanyuk, A.; Rebek, J., Jr. Chem. Commun. 2001, 2424-2425.
21. (d) Clyde-Watson, Z.; Vidal-Ferran, A.; Twyman, L. J.; Walter, C. J.; McCallien, S.; Fanni. D. W. J.; Bampos, N.; Wylie, R. S.; Sanders, J. K. M. New J. Chem. 1998, 22, 493-502.
22. (e) Kim, H.-J.; Heo, J.; Jeon, W. S.; Lee, E.; Kim, J.; Sakamoto, S.; Yamaguchi, K.; Kim, K. Angew. Chem., Int. Ed. 2001, 40, 1526-1529.
23. (f) Chopra, N.; Naumann, C.; Sherman, J. C. Angew. Chem., Int. Ed. 2001, 39, 194-196.
24. Shivanyuk, A.; Rebek, J., Jr. J. Am. Chem. Soc. 2002, 124, 12074-12075.
25. Shivanyuk, A.; Rebek, J., Jr. Angew. Chem., Int. Ed. 2003, 42, 684-686.
26. Chen, J.; Rebek, J., Jr. Org. Lett. 2002, 4, 327-329. Yoshizawa, M.; Takeyama, Y.; Okano, T.; Fujita, M. J. Am. Chem. Soc. 2003, 125, 3243-3247.
27. Chen, J.; Rebek, J., Jr. Org. Lett. 2002, 4, 327-329. Yoshizawa, M.; Takeyama, Y.; Okano, T.; Fujita, M. J. Am. Chem. Soc. 2003, 125, 3243-3247.
28. Mecozzi, S.; Rebek, J., Jr. Chem.-Eur. J. 1998, 4, 1016-1022.
29. Heinz, T.; Rudkevich, D. M.; Rebek, J., Jr. Angew. Chem., Int. Ed. 1999, 38, 1136-1139.
30. Graf, E.; Graff, R.; Hosseini, M. W.; Huguenard, C.; Taulelle, F. Chem. Commun. 1997, 1458-1460.
31. Shivanyuk, A.; Scarso, A.; Rebek, J., Jr. Chem. Commun. 2003, in press.
32. Körner, S. K.; Tucci. F. C.; Rudkevich, D. M.; Heinz, T.; Rebek, J., Jr. Chem.-Eur. J. 2000, 6, 187-195.
33. Under these conditions, 2-chlorobutane, 2-butanol, and 2-pentanol all form encapsulation complexes with two guests inside. The complexes are diastereomeric: one meso-form including two guests of opposite handedness and those with two molecules of (R)- or (S)-2-butanol. The diastereomeric capsules are formed in equal amounts
34. Rebek, J., Jr.; Askew, B.; Doa, M.; Ballester, P. J. Ant. Chem. Soc. 1987, 109, 4119-4120.
35. 3 doublet δ = -1.74 and -1.87. Δδ = -2.79 and -2.82.
36. () Hyperchem, Release 7; Hyper cube Inc., 2002.
37. Hayashida, O.; Sebo, L.; Rebek, J., Jr. J. Org. Chem. 2002, 67, 8291-8298.