Asymmetric crystallization of bisguanidinobenzene derivatives

Tetrahedron Letters

Volumn 48, Issue 48, 2007, Pages 8526-8530

  Nakanishi, Waka ^a   Ogino, Akiko ^a   Kawahata, Masatoshi ^b   Yamaguchi, Kentaro ^b   Ishikawa, Tsutomu ^a  

^a CHIBA UNIVERSITY   (Japan)

^b TOKUSHIMA BUNRI UNIVERSITY   (Japan)

Author keywords

Asymmetric crystallization; CD; Guanidine; X ray diffraction

Indexed keywords

ALEXIDINE; BENZENE DERIVATIVE; BISGUANIDINOBENZENE DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; ASYMMETRIC SYNTHESIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; CIRCULAR DICHROISM; CRYSTAL STRUCTURE; CRYSTALLIZATION; METHYLATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTON TRANSPORT; X RAY CRYSTALLOGRAPHY;

EID: 35649024856     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.09.144     Document Type: Article

References (34)

1. Azumaya I., Yamaguchi K., Okamoto I., Kagechika H., and Shudo K. J. Am. Chem. Soc. 117 (1995) 9083
2. Azumaya I., Kato T., Okamoto I., Yamasaki R., Tanatani A., Yamaguchi K., Kagechika H., and Takayanagi H. Org. Lett. 5 (2003) 3939
3. Tanatani A., Yamaguchi K., Azumaya I., Fukutomi R., Shudo K., and Kagechika H. J. Am. Chem. Soc. 120 (1998) 6433
4. Sakamoto M., Unosawa A., Kobaru S., Saito A., Mino T., and Fujita T. Angew. Chem., Int. Ed. 44 (2005) 5523
5. For reviews, see:. Feringa B.L., and Delden R.A. Angew. Chem., Int. Ed. 38 (1999) 3418
6. Griesbeck A.G., and Meierhenrich U.J. Angew. Chem., Int. Ed. 41 (2002) 3417
7. Costa M., Chiusoli G.P., Taffurelli D., and Dalmonego G. J. Chem. Soc., Perkin Trans. 1 (1998) 1541
8. Kovačević B., and Maksić Z.B. Chem. Eur. J. 8 (2002) 1694
9. For example:. Alcazar V., Segure M., Prados P., and Mendoza J. Tetrahedron Lett. 39 (1998) 1033
10. Isobe T., Fukuda K., and Ishikawa T. Tetrahedron: Asymmetry 9 (1998) 1729
11. Isobe T., Fukuda K., Araki Y., and Ishikawa T. Chem. Commun. (2001) 243
12. Ishikawa T., Araki Y., Kumamoto T., Seki H., Fukuda K., and Isobe T. Chem. Commun. (2001) 245
13. Hada K., Watanabe T., Isobe T., and Ishikawa T. J. Am. Chem. Soc. 123 (2001) 7705
14. Ishikawa T., and Isobe T. Chem. Eur. J. 8 (2002) 552
15. Kitani Y., Kumamoto T., Isobe T., Fukuda K., and Ishikawa T. Adv. Synth. Catal. 347 (2005) 1653
16. Wannaporn D., and Ishikawa T. Mol. Divers. 9 (2005) 321
17. Kumamoto T., Ebine K., Endo M., Araki Y., Fushimi Y., Miyamoto I., Ishikawa T., Isobe T., and Fukuda K. Heterocycles 66 (2005) 347
18. Haga T., and Ishikawa T. Tetrahedron 61 (2005) 2857
19. Wannaporn D., and Ishikawa T. J. Org. Chem. 70 (2005) 9399
20. Wannaporn D., Ishikawa T., Kawahata M., and Yamaguchi K. J. Org. Chem. 71 (2006) 6600
21. Kawahata M., Yamaguchi K., and Ishikawa T. Cryst. Growth Des. 5 (2005) 373
22. Kawahata M., Shikii K., Seki H., Ishikawa T., and Yamaguchi K. Chem. Pharm. Bull. 54 (2006) 147
23. The chiral crystals were obtained by complexation of bisguanidinobenzene 1 and (2S,3S)-(+)-O,O′-dibenzoyltartaric acid. In these crystals, only one enantiomer of the trans form of 1 exists. Surprisingly, the chiral crystal was also obtained from the complex of 1 and achiral benzoic acid and water. In these crystals, the complex formed a helical supermolecule carrying only the trans enantiomer of 1. The chirality disappeared when the crystal was dissolved in a solvent. These results will be reported elsewhere in the near future.
24. Isobe T., and Ishikawa T. J. Org. Chem. 64 (1999) 5832
25. Isobe T., and Ishikawa T. J. Org. Chem. 64 (1999) 6984
26. Isobe T., and Ishikawa T. J. Org. Chem. 64 (1999) 6989
27. Figee A., Altenbach H.J., Brauer D.J., and Tielmann P. Tetrahedron: Asymmetry 13 (2002) 137-144
28. Details of the crystal structure analyses are provided as Supplementary data. CCDC 654529 (1), CCDC 654532 (2a), CCDC 654536 (P-2b), CCDC 654531 (M-2b), CCDC 654530 (M-2c recrystallized from MeOH), CCDC 654535 (P-2c), CCDC 654534, (M-2c), and CCDC 654533 (2d) contain the supplementary crystallographic data for this Letter. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
29. Flack H.D. Acta Crystallogr. Sect. A (1983) 39 876
30. Attempts to synthesize dialkylated bisguanidinobenzene were not successful. Treatment of N,N′-dimethyl-o-diaminobenzene with 4 afforded an undesired product through intermolecular reactions.
31. Nakanishi W., Ishikawa T., and Margetić D. Bull. Chem. Soc. Jpn. 80 (2007) 1187
32. From dynamic studies on guanidines, it is known that both the C{double bond, long}N and Ar-N bonds rapidly rotate at rt. See:. Kessler H., and Leibfritz D. Tetrahedron Lett. 6 (1969) 427
33. Kessler H., and Leibfritz D. Tetrahedron 25 (1969) 5127
34. Kessler H., and Leibfritz D. Tetrahedron 26 (1970) 1805