Pseudotetrahedral polyhaloadamantanes as chirality probes: Synthesis, separation, and absolute configuration

Journal of the American Chemical Society

Volumn 124, Issue 45, 2002, Pages 13348-13349

  Schreiner, Peter R ^a,b   Fokin, Andrey A ^c   Lauenstein, Oliver ^d   Okamoto, Yoshio ^e   Wakita, Tsuneki ^e   Rinderspacher, Christopher ^b   Robinson, Gregory H ^b   Vohs, Jason K ^b   Campana, Charles F ^f  

^a JUSTUS LIEBIG UNIVERSITY   (Germany)

^b UNIVERSITY OF GEORGIA   (United States)

^c NATIONAL TECHNICAL UNIVERSITY OF UKRAINE   (Ukraine)

^d UNIVERSITY OF GÖTTINGEN   (Germany)

^e NAGOYA UNIVERSITY   (Japan)

^f BRUKER AXS INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ADAMANTANE DERIVATIVE; HALIDE; POLYMER;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; CHIRALITY; CIRCULAR DICHROISM; MOLECULAR PROBE; STEREOCHEMISTRY; SYNTHESIS;

EID: 0037073232     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0274195     Document Type: Article

References (33)

1. Crassous, J.; Collet, A. Enantiomer 2000, 5, 429-438.
2. Swarts, F. F. Bull. Acad. R. Belg. 1896, 31, 28.
3. Swarts, F. F. Bull. Acad. R. Belg. 1893, 26, 102.
4. Grosenick, H.; Schurig, V.; Costante, J.; Collet, A. Tetrahedron: Asymmetry 1995, 6, 87-88.
5. Canceill, J.; Lacombe, L.; Collet, A. J. Am. Chem. Soc. 1985, 107, 6993-6996.
6. Wilen, S. H.; Bunding, K. A.; Kascheres, C. M.; Wieder, M. J. J. Am. Chem. Soc. 1985, 107, 6997-6998.
7. Costante, J.; Hecht, L.; Polavarapu, P. L.; Collet, A.; Barron, L. D. Angew. Chem., Int. Ed. Engl. 1997, 36, 885-887.
8. Doyle, T. R.; Vogl, O. J. Am. Chem. Soc. 1989, 111, 8510-8511.
9. Anderson, P. H.; Stephenson, B.; Mosher, H. S. J. Am. Chem. Soc. 1974, 96, 3171-3177.
10. Novak, I.; Li, D. B. J. Phys. Chem. 2002, 106, 465-468.
11. Fokin, A. A.; Lauenstein, O.; Gunchenko, P. A.; Schreiner, P. R. J. Am. Chem. Soc. 2001, 123, 1842-1847.
12. Applequist, J.; Rivers, P.; Applequist, D. E. J. Am. Chem. Soc. 1969, 91, 5705-5709.
13. Stepanov, F. N.; Smirnova, N. A.; Baldan, V. F.; Yurchenko, A. G. Zh. Org. Khim. 1974, 10, 234-239.
14. Bouchiat, M. A.; Bouchiat, C. Rep. Prog. Phys. 1997, 60, 1351-1396.
15. Quack, M.; Stohner, J. Chirality 2001, 13, 745-753.
16. Berger, R.; Quack, M. ChemPhysChem 2000, 1, 57-60.
17. Berger, R.; Quack, M.; Tschumper, G. S. Helv. Chim. Acta 2000, 83, 1919-1950.
18. Quack, M. Chem. Phys. Lett. 1986, 132, 147-153.
19. Quack, M. Angew. Chem., Int. Ed. 2002, in press.
20. Barluenga, J.; Gonzalez-Bobes, F.; Gonzalez, J. M. Angew. Chem., Int. Ed. 2002, 41, 2556-2558.
21. Schreiner, P. R.; Lauenstein, O.; Butova, E. D.; Gunchenko, P. A.; Kolomitsin, I. V.; Wittkopp, A.; Feder, G.; Fokin, A. A. Chem.-Eur. J. 2001, 7, 4996-5003.
22. Schreiner, P. R.; Lauenstein, O.; Butova, E. D.; Fokin, A. A. Angew. Chem., Int. Ed. 1999, 38, 2786-2788.
23. Schreiner, P. R.; Lauenstein, O.; Kolomitsyn, I. V.; Nadi, S.; Fokin, A. A. Angew. Chem., Int. Ed. 1998, 37, 1895-1897.
24. Liguori, L.; Bjorsvik, H. R.; Bravo, A.; Fontana, F.; Minisci, F. Chem. Commun. 1997, 1501-1502.
25. Details on the crystal structure determination can be found in the Supporting Information. Final coordinates are deposited in the Cambridge Crystallographic Database (CCDC 185398) and are available from there free of charge.
26. Okamoto, Y.; Yashima, E. Angew. Chem., Int. Ed. 1998, 37, 1020-1043.
27. Furche, F.; Ahlrichs, R.; Wachsmann, C.; Weber, E.; Sobanski, A.; Vögtle, F.; Grimme, S. J. Am. Chem. Soc. 2000, 122, 1717-1724.
28. All structures were optimized and characterized as minima (frequency analysis) with Gaussian 98 Rev. A.9 (Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98; Gaussian, Inc.: Pittsburgh, PA, 1998) using the B3LYP functional (Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652) and a 6-31+G** basis set. The chiroptical properties were computed with the Turbomole program package (AhLrichs, R.; B̈r, M.; Häser, M.; Horn, H.; Kölmel, C. Chem. Phys. Lett. 1989, 162, 3) utilizing a TZVP basis set and the B3LYP functional.
29. All structures were optimized and characterized as minima (frequency analysis) with Gaussian 98 Rev. A.9 (Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98; Gaussian, Inc.: Pittsburgh, PA, 1998) using the B3LYP functional (Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652) and a 6-31+G** basis set. The chiroptical properties were computed with the Turbomole program package (AhLrichs, R.; B̈r, M.; Häser, M.; Horn, H.; Kölmel, C. Chem. Phys. Lett. 1989, 162, 3) utilizing a TZVP basis set and the B3LYP functional.
30. All structures were optimized and characterized as minima (frequency analysis) with Gaussian 98 Rev. A.9 (Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98; Gaussian, Inc.: Pittsburgh, PA, 1998) using the B3LYP functional (Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652) and a 6-31+G** basis set. The chiroptical properties were computed with the Turbomole program package (AhLrichs, R.; B̈r, M.; Häser, M.; Horn, H.; Kölmel, C. Chem. Phys. Lett. 1989, 162, 3) utilizing a TZVP basis set and the B3LYP functional.
31. Ribe, S.; Kondru, R. K.; Beratan, D. N.; Wipf, P. J. Am. Chem. Soc. 2000, 122, 4608-4617.
32. Kondru, R. K.; Wipf, P.; Beratan, D. N. Science 1998, 282, 2247-2250.
33. Stephens, P. J.; Devlin, F. J.; Cheeseman, J. R.; Frisch, M. J.; Mennucci, B.; Tomasi, J. Tetrahedron: Asymmetry 2000, 11, 2443-2448.