Chiral discrimination of 2-arylalkanoic acids by (1S,2R)-1-aminoindan-2-ol through the formation of a consistent columnar supramolecular hydrogen-bond network

Journal of the Chemical Society. Perkin Transactions 2

Volumn , Issue 1, 2000, Pages 111-119

  Kinbara, Kazushi ^a   Kobayashi, Yuka ^a   Saigo, Kazuhiko ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; AMMONIUM COMPOUNDS; CONFORMATIONS; HYDROGEN BONDS; X RAY CRYSTALLOGRAPHY;

ARYLALKANOIC ACIDS; CARBOXYLATE; CHIRAL DISCRIMINATION; DIASTEREOMERIC SALTS; RACEMIC ACIDS;

ORGANIC COMPOUNDS;

EID: 0033993077     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/a905566e     Document Type: Article

References (29)

1. J. Jacques, A. Collet and S. H. Wilen, Enantiomers, Racemates, and Resolutions; Krieger Publishing Company, Malabar, Florida, 1994.
2. For examples of novel resolving agents, see: A. D. van der Haest, H. Wynberg, F. J. J. Leusen and A. Bruggink, Recl. Trav. Chim. Pays-Bas, 1993, 112, 230
3. D. Kozma, M. Acs and E. Fogassy, Tetrahedron, 1994, 50, 6907
4. B. Eric and M. Moudachirou, Tetrahedron, 1994, 50, 10309
5. M. Pallavicini, E. Valoti, L. Villa and O. Piccolo, Tetrahedron: Asymmetry, 1996, 7, 1117.
6. K. Kinbara, Y. Kobayashi and K. Saigo, J. Chem. Soc., Perkin Trans. 2, 1998, 1767.
7. T. Manimaran and A. A. Potter, US Patent 5,162,576, 1992.
8. 6,7 In the present study, instead of optimisation, we adjusted the quantity and ratio of the mixed solvent so that the resolving efficiency was as high as possible.
9. E. Fogassy, F. Faigl and M. Ács, Tetrahedron, 1985, 41, 2837
10. F. J. J. Leusen, J. H. Noordik and H. R. Karfunkel, Tetrahedron, 1985, 49, 5377
11. D. Kozma, G. Pokol and M. Ács, J. Chem. Soc., Perkin Trans. 2, 1992, 435
12. E. Collet in Comprehensive Supramolecular Chemistry, D. N. Reinhoudt, ed., Pergamon, Oxford, 1996, vol. 1, pp. 113-149
13. E. J. Ebbers, B. J. M. Plum, G. J. A. Ariaans, B. Kaptein, Q. B. Broxterman, A. Bruggink and B. Zwanenburg, Tetrahedron: Asymmetry, 1997, 8, 4047
14. E. Ebbers, G. J. A. Ariaans, B. Zwanenburg and A. Bruggink, Tetrahedron: Asymmetry, 1998, 9, 2745.
15. J. Viret, H. Patzelt and A. Collet, Tetrahedron Lett., 1986, 27, 5865
16. T. Shiraiwa, Y. Sado, S. Fujii, M. Nakamura and H. Kurokawa, Bull. Chem. Soc. Jpn., 1987, 60, 824.
17. 3.
18. K. Kinbara, Y. Hashimoto, Y. Sukegawa, H. Nohira and K. Saigo, J. Am. Chem. Soc., 1996, 118, 3441.
19. A table of N...O and O...O distances in the diastereomeric salts of (1S,2R)-2 with 3-7 is deposited as supporting information (Table S1).
20. Concerning the favorable location of hydrogens around hydrogen acceptors, see: R. Taylor and O. Kennard, Acc. Chem. Res., 1984, 17, 320
21. J. P. Glusker, Mol. Cryst. Liq. Cryst., 1992, 211, 75.
22. A. Gavezzotti and G. R. Desiraju, Acta. Crystallogr., Sect. B, 1988, 44, 427
23. G. R. Desiraju and A. Gavezzotti, Acta. Crystallogr., Sect. B. 1989, 45, 473.
24. A table of the angles and lengths between the stacking aromatic rings is deposited as supporting information (Table S2 and Table S3).
25. M. Nishio, M. Hirota and Y. Umezawa, CH...π Interaction: Evidence, Nature, and Consequences, Wiley-VCH Publication: Weinheim, Berlin, 1998.
26. L. J. Bellamy and R. J. Pace, Spectrochim. Acta, 1969, 25, 319.
27. G. R. Desiraju, Angew. Chem., Int. Ed. Engl., 1995, 34, 2311.
28. CRYSTAN GM, A Computer Program for the Solution and Refinement of Crystal Structures for X-ray Diffraction Data (MAC Science Corporation).
29. A. Altomare, G. Cascarano, C. Giacovazzo and A. Guagliardi, J. Appl. Crystallogr., 1993, 26, 343.