Synthesis and structural features of cyclobutane-containing chiral bicyclic ureas

Tetrahedron Asymmetry

Volumn 21, Issue 3, 2010, Pages 339-345

  Gorrea, Esther ^a   Nolis, Pau ^a   Álvarez Larena, Ángel ^a   Silva, Eric Da ^a   Branchadell, Vicenç ^a   Ortuño, Rosa M ^a  

^a UNIVERSITAT AUTÒNOMA DE BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CARBAMIC ACID DERIVATIVE; CARBONYL DERIVATIVE; CYCLOBUTANE; UREA DERIVATIVE;

ARTICLE; CALCULATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; CRYSTAL STRUCTURE; ENANTIOMER; ENERGY TRANSFER; HYDROGEN BOND; INFRARED RADIATION; MOLECULAR INTERACTION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; SOLID STATE; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS; TRANSMISSION ELECTRON MICROSCOPY; X RAY ANALYSIS;

EID: 77949301206     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2010.01.020     Document Type: Article

References (35)

1. Matsuo J., Okano M., Takeuchi K., Tanaka H., and Ishibashi H. Tetrahedron: Asymmetry 18 (2007) 1906
2. Govindaraju T., Kumar V.A., and Ganesh K.N. J. Org. Chem. 69 (2004) 1858
3. For some examples, see:. Palma C., Nardelli F., and Manzini S. Eur. J. Pharm. 374 (1999) 435
4. Meini S., Bellucci F., Catalani C., Cucchi P., Patacchini R., Rotondaro L., Altamura M., Giuliani S., Giolitti A., and Maggi C.A. Eur. J. Pharm. 488 (2004) 61
5. Chen Z., Goehring R.R., Valenzano K.Z., and Kyle D.J. Bioorg. Med. Chem. Lett. 14 (2004) 1347
6. Mogil J.S., Grisel J.E., Reinscheid R.K., Civelli O., Belknap J.K., and Grandy D.K. Neuroscience (Oxford) 75 (1996) 333
7. Calo G., Rizzi A., Bogoni R., Guerrini R., Salvadori S., and Regoli D. Clin. Exp. Pharmacol. Physiol. 29 (2002) 223
8. Methot J.L., Dunstan T.A., Mampreian D.M., Adams B., and Altman M.D. Tetrahedron Lett. 49 (2008) 1155
9. For some leading references, see:. Yabuuchi K., Marfo-Owusu E., and Kato T. Org. Biomol. Chem. 1 (2003) 3464
10. Violette A., Averlant-Petit M.C., Semetey V., Hemmerlin C., Casimir R., Graff R., Marraud M., Briand J.P., Rognan D., and Guichard G. J. Am. Chem. Soc. 127 (2005) 2156
11. Clayden J., Lemiègre L., Morris G.A., Pickworth M., Snape T.J., and Jones L.H. J. Am. Chem. Soc. 130 (2008) 15193
12. Fisher L., Didierjean C., Jolibois F., Semetey V., Lozano J.M., Briand J.P., Marraud M., Poteau R., and Guichard G. Org. Biomol. Chem. 6 (2008) 2596
13. Rodriguez J.M., and Hamilton A.D. Angew. Chem., Int. Ed. 46 (2007) 8614
14. Van Gorp J.J., Vekemans J.A.J.M., and Meijer E.W. J. Am. Chem. Soc. 124 (2002) 14759
15. Karatchevtseva I., Cassidy D.J., Wong Chi Man M., Mitchell D.R.G., Hanna J.V., Carcel C., Bied C., Moreau J.J.E., and Bartlett J.R. Adv. Funct. Mater. 17 (2007) 3926
16. Custelcean R. Chem. Commun. (2008) 295
17. Izquierdo S., Kogan M.J., Parella T., Moglioni A.G., Branchadell V., Giralt E., and Ortuño R.M. J. Org. Chem. 69 (2004) 5093
18. Izquierdo S., Rúa F., Sbai A., Parella T., Álvarez-Larena A., Branchadell V., and Ortuño R.M. J. Org. Chem. 70 (2005) 7963
19. Rúa F., Boussert S., Parella T., Díez-Pérez I., Branchadell V., Giralt E., and Ortuño R.M. Org. Lett. 9 (2007) 3643
20. Torres E., Acosta-Silva C., Rúa F., Álvarez-Larena A., Parella T., Branchadell V., and Ortuño R.M. Tetrahedron 65 (2009) 5669
21. Torres E., Gorrea E., Da Silva E., Nolis P., Branchadell V., and Ortuño R.M. Org. Lett. 11 (2009) 2301
22. Torres E., Gorrea E., Burusco K.K., Da Silva E., Nolis P., Rúa F., Boussert S., Díez-Pérez I., Dannenberg S., Izquierdo S., Giralt E., Jaime C., Branchadell V., and Ortuño R.M. Org. Biomol. Chem. 8 (2010) 564
23. Martín-Vilà M., Muray E., Aguado G.P., Álvarez-Larena A., Branchadell V., Minguillón C., Giralt E., and Ortuño R.M. Tetrahedron: Asymmetry 11 (2000) 3569
24. Brand T., Cabrita E.J., and Berger S. Prog. NMR Spectrosc. 46 (2005) 159
25. Deschamps J.R., George C., Gilardi R.D., Gagnon J.L., and Zajac W.W. Acta Crystallogr., Sect. C 52 (1996) 993
26. Reisinger A., Koch R., Bernhardt P.V., and Wentrup C. Org. Biomol. Chem. 2 (2004) 1227
27. Jeffrey G.A., and Lewis L. Carbohydr. Res. 60 (1978) 179
28. Wu D., Chen A., and Johnson Jr. C.S. J. Magn. Reson., Ser. A 115 (1995) 260
29. Sheldrick, G. M. shelxs97/shelxl97, University of Göttingen, Germany.
30. 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.; Bakken, V.; 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 E.01 Gaussian, Inc.: Wallingford CT, 2004.
31. Zhao Y., Schultz N.E., and Truhlar D.G. J. Chem. Theor. Comput. 2 (2006) 364
32. Hehre W.J., Radom L., Schleyer P.v.R., and Pople J.A. Ab Initio Molecular Orbital Theory (1986), Wiley, New York
33. Klamt A., and Schüürmann G. J. Chem. Soc., Perkin Trans. 2 (1993) 799
34. Barone V., and Cossi M. J. Phys. Chem. A 102 (1998) 1995
35. Cossi M., Rega N., Scalmani G., and Barone V. J. Comput. Chem. 24 (2003) 669