Synthesis and chiroptical properties of cryptophanes having C 1-symmetry

Journal of Organic Chemistry

Volumn 73, Issue 1, 2008, Pages 66-75

  Cavagnat, Dominique ^a   Buffeteau, Thierry ^a   Brotin, Thierry ^b  

^a INSTITUT DES SCIENCES MOLÉCULAIRES   (France)

^b UNIVERSITÉ DE LYON   (France)

Author keywords

[No Author keywords available]

Indexed keywords

DENSITY FUNCTIONAL THEORY; DICHROISM; SOLVENTS; SPECTROSCOPIC ANALYSIS; SYNTHESIS (CHEMICAL);

AB INITIO CALCULATIONS; CHIROPTICAL PROPERTIES; ELECTRONIC CIRCULAR DICHROISM; VIBRATIONAL CIRCULAR DICHROISM;

ORGANIC COMPOUNDS;

CROWN COMPOUND; CRYPTOPHANE A; CRYPTOPHANE DERIVATIVE; UNCLASSIFIED DRUG;

AB INITIO CALCULATION; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CHIRALITY; CIRCULAR DICHROISM; STRUCTURE ANALYSIS; SUPRAMOLECULAR CHEMISTRY; SYNTHESIS;

EID: 37549064648     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo701662w     Document Type: Article

References (31)

1. Collet, A. Tetrahedron 1987, 43, 5725-5759.
2. (a) Canceill, J.; Césario, M.; Collet, A.; Guilhem, J.; Lacombe, L.; Lozach, B.; Pascard, C. Angew. Chem., Int. Ed. Engl. 1989, 28, 9, 1246-1248.
3. (b) Garel, L.; Dutasta, J.-P.; Collet, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 8, 1169-1171.
4. (c) Bartik, K.; Luhmer, M.; Dutasta, J.-P.; Collet, A.; Reisse, J. J. Am. Chem. Soc. 1998, 120, 784-791.
5. (d) Brotin, T.; Lesage, A.; Emsley, L.; Collet, A. J. Am. Chem. Soc. 2000, 122, 1171-1174.
6. (e) Brotin, T.; Dutasta, J.-P. Eur. J. Org. Chem. 2003, 973-984.
7. (a) Canceill, J.; Lacombe, L.; Collet, A. J. Am. Chem. Soc. 1985, 107, 6993-6996.
8. (b) Crassous, J.; Collet, A. Enantiomer 2000, 5, 429-438.
9. Canceill, J.; Collet, A.; Gotarelli, G.; Palmieri, P. J. Am. Chem. Soc. 1987, 109, 6454-6464.
10. (a) Nafie, L. A.; Dukor, R. K.; Freedmann, T. B. In Handbook of Vibrational Spectroscopy; Chalmers, J. M., Griffiths, P. R., Eds.; John Wiley & Sons: Chichester, UK, 2002; Vol. 1, pp 731-744.
11. (b) Freedman, T. B.; Cao, X.; Dukor, R. K.; Nafie, L. A. Chirality 2003, 15, 743-758 and references therein.
12. Stephens, P. J.; Delvin, F. J. Chirality 2000, 12, 172-179.
13. Urbanova, M.; Setnicka, V.; Delvin, F. J.; Stephens, P. J. J. Am. Chem. Soc. 2005, 127, 6700-6711.
14. (a) Buffeteau, T.; Ducasse, L.; Poniman, L.; Delsuc, N.; Huc, I. Chem. Commun. 2006, 2714-2716.
15. (b) Ducasse, L.; Castet, F.; Fritsch, A.; Huc, I.; Buffeteau, T. J. Phys. Chem. A 2007, 111, 5092-5098.
16. Brotin, T.; Cavagnat, D.; Dutasta, J.-P.; Buffeteau, T. J. Am. Chem. Soc. 2006, 128, 5533-5540.
17. Brotin, T.; Barbe, R.; Darzac, M.; Dutasta, J.-P. Chem. - Eur. J. 2003, 9, 5784-5792.
18. Darzac, M.; Brotin, T.; Bouchu, D.; Dutasta, J.-P. Chem. Commun. 2002, 48-49.
19. 3/ethanol affords pure 1a (25%). Evaporation of the filtrate, followed by hydrolysis under basic condition, gives rise to enantioenriched (+)-cryptophanol 2, which can be used for subsequent reaction with (+)-camphanic acid chloride. A similar treatment performed with this diastereomer gives rise to optically pure diastereomer 1b in similar yield.
20. Spence, M. M.; Ruiz, E. J.; Rubin, S. M.; Lowery, T. L.; Winssinger, N.; Schultz, P. G.; Wemmer, D. E.; Pines, A. J. Am. Chem. Soc. 2004, 126, 15287-15294.
21. (a) Sáa, J. M.; Dopico, M.; Martorell, G.; Garcia-raso, A. J. Org. Chem. 1990, 55, 991-995.
22. (b) Lipshutz, B. H.; Buzard, D. J.; Vivian, R. W. Tetrahedron Lett. 1999, 40, 6871-6874.
23. (c) Sajiki, H.; Mori, A.; Mizusaki, T.; Ikawa, T.; Maegawa, T.; Hirota, K. Org. Lett. 2006, 8, 5, 987-990.
24. (a) Canceill, J.; Collet, A. J. Chem. Soc., Chem. Commun. 1988, 582-584.
25. (b) Collet, A.; Dutasta, J.-P.; Lozach, B. Bull. Soc. Chim. Belg. 1990, 99, 617-633.
26. Platt, J. R. J. Chem. Phys. 1951, 19, 263-271.
27. Buffeteau, T.; Lagugné-Labarthet, F.; Sourrisseau, C. Appl. Spectrosc 2005, 59, 732-745.
28. Nafie, L. A.; Vidrine, D. W. In Fourier Transform Infrared Spectroscopy; Basile, J. R., Basile, L. J., Eds.; Academic Press: New York, 1982; Vol. 3, pp 83-123.
29. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, revision B.04; Gaussian Inc.: Pittsburgh, PA, 2003.
30. Cheeseman, J. R.; Frisch, M. J.; Delvin, F. J.; Stephens, P. J. Chem. Phys. Lett. 1996, 252, 211-220.
31. Darzac, M.; Brotin, T.; Rousset-Arzel, L.; Bouchu, D.; Dutasta, J.-P. New J. Chem. 2004, 28, 502-512.