A practical approach to the resolution of racemic N-benzyl α-amino acids by liquid-liquid extraction with a lipophilic chiral salen-cobalt(III) complex

Angewandte Chemie - International Edition

Volumn 45, Issue 15, 2006, Pages 2449-2453

  Reeve, Toby B ^a   Cros, Jean Philippe ^a   Gennari, Cesare ^a   Piarulli, Umberto ^b   De Vries, Johannes G ^c  

^a CNR   (Italy)

^b UNIVERSITY OF INSUBRIA   (Italy)

^c DSM Pharmaceutical Products   (Netherlands)

Author keywords

Amino acids; Chiral resolution; Cobalt; Molecular recognition; N,O ligands

Indexed keywords

CHIRAL RESOLUTION; MOLECULAR RECOGNITION; N,O LIGANDS;

COBALT COMPOUNDS; EXTRACTION; MOLECULAR DYNAMICS; REACTION KINETICS; REDUCTION;

AMINO ACIDS;

AMINO ACID; BENZENE; COBALT; ETHYLENEDIAMINE DERIVATIVE; LIPID; N,N' DISALICYLIDENEETHYLENEDIAMINE;

ARTICLE; CHEMICAL PHENOMENA; CHEMICAL STRUCTURE; CHEMISTRY; HYDROPHOBICITY; STEREOISOMERISM;

AMINO ACIDS; BENZENE; COBALT; ETHYLENEDIAMINES; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; HYDROPHOBICITY; LIPIDS; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 33746317330     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200504116     Document Type: Article

References (43)

1. a) P. Breccia, M. Van Gool, R. Perez-Fernandez, S. Martin-Santamaria, F. Gago, P. Prados, J. De Mendoza, J. Am. Chem. Soc. 2003, 125, 8270-8284;
2. b) X. X. Zhang, J. S. Bradshaw, R. M. Izatt, Chem. Rev. 1997, 97, 3313-3361.
3. a) P. D. Knight, P. Scott, Coord. Chem. Rev. 2003, 242, 125-143, and references therein;
4. b) H.-J. Kim, R. Asif, D. S. Chung, J.-I. Hong, Tetrahedron Lett. 2003, 44, 4335-4338;
5. c) H.-J. Kim, W. Kim, A. J. Lough, B. M. Kim, J. Chin, J. Am. Chem. Soc. 2005, 127, 16 776-16 777.
6. a) R. R. Fenton, F. S. Stephens, R. S. Vagg, P. A. Williams, Inorg. Chim. Acta 1995, 236, 109-115;
7. b) J. Chin, S. S. Lee, K. J. Lee, S. Park, D. H. Kim, Nature 1999, 401, 254-257.
8. a) W. Linder, J. N. LePage, G. Davies, D. E. Seitz, B. L. Karger, J. Chromatogr. 1979, 185, 323-344;
9. b) E. Gil-Av, A. Tishbee, P. E. Hare, J. Am. Chem. Soc. 1980, 102, 5115-5117;
10. c) E. Armani, L. Barazzoni, A. Dossena, R. Marchelli, J. Chromatogr. 1988, 441, 287-298, and references therein;
11. d) T. Arai, H. Koike, K. Hirota, H. Oizumi, J. Chromatogr. 1988, 448, 439-444;
12. e) N. Ôi, H. Kitahara, R. Kira, J. Chromatogr. 1992, 592, 291-296;
13. f) N. Oi, H. Kitahara, F. Aoki, J. Chromatogr. A 1995, 707, 380-383;
14. g) G. Galaverna, R. Corradini, A. Dossena, E. Chiavaro, R. Marchelli, F. Dallavalle, G. Folesani, J. Chromatogr. A 1998, 829, 101-113.
15. a) P. Scrimin, U. Tonellato, N. Zanta, Tetrahedron Lett. 1988, 29, 4967-4970;
16. b) P. Scrimin, P. Tecilla, U. Tonellato, Tetrahedron 1995, 51, 217-230;
17. c) P. J. Pickering, J. B. Chaudhuri, J. Membr. Sci. 1997, 127, 115-130;
18. d) B. Baragaña, A. G. Blackburn, P. Breccia, A. P. Davis, J. de Mendoza, J. M. Padrón-Carrillo, P. Prados, J. Riedner, J. G. de Vries, Chem. Eur. J. 2002, 8, 2931-2936;
19. e) J. D. Clark, B. Han, A. S. Bhown, S. R. Wickramasinghe, Sep. Purif. Technol. 2005, 42, 201-211.
20. T. J. M. De Bruin, A. T. M. Marcelis, H. Zuilhof, L. M. Rodenburg, H. A. G. Niederländer, A. Koudijs, P. E. M. Overdevest, A. van der Padt, E. J. R. Sudhölter, Chirality 2000, 12, 627-636.
21. A. L. Creagh, B. B. E. Hasenack, A. van der Padt, E. J. R. Sudholter, K. van't Riet, Biotechnol. Bioeng. 1994, 44, 690-698.
22. Y. Fujii, M. Matsufuru, A. Saito, S. Tsuchiya, Bull. Chem. Soc. Jpn. 1981, 54, 2029-2038.
23. III(ent-1)(N-Bn-Ala)]) and the uncomplexed amino acid, respectively (see Ref. [8]).
24. a) T. Takeuchi, R. Horikawa, T. Tanimura, Anal. Chem. 1984, 56, 1152-1155;
25. b) T. Takeuchi, R. Horikawa, T. Tanimura, Y. Kabasawa, Sep. Sci. Technol. 1990, 25, 941-951;
26. c) H. Nishizawa, K. Tahara, A. Hayashida, Y. Abe, Anal. Sci. 1993, 9, 611-615;
27. d) H. Tsukube, J. Uenishi, T. Kanatani, H. Itoh, O. Yonemitsu, Chem. Commun. 1996, 477-478;
28. e) H. Tsukube, S. Shinoda, J. Uenishi, T. Kanatani, H. Itoh, M. Shiode, T. Iwachido, O. Yonemitsu, Inorg. Chem. 1998, 37, 1585-1591;
29. f) S. E. Snyder, J. R. Carey, W. H. Pirkle, Tetrahedron 2005, 61, 7562-7567.
30. 4), see: I. L. Lysenko, O. G. Kulinkovich, Russ. J. Org. Chem. 2001, 37, 1238-1243;
31. b) for the preparation of enzyme inhibitors, see: C. T. Supuran, A. Scozzafava, Eur. J. Pharm. Sci. 2000, 10, 67-76;
32. c) for the synthesis of 2,3,4-trisubstituted piperidines, see: S. Laschat, R. Fröhlich, B. Wibbeling, J. Org. Chem. 1996, 61, 2829-2838;
33. d) for the synthesis of Staline and hydroxymethylene dipeptide isosteres, see: A. McCluskey, J. Garner, D. J. Young, S. Caballero, Tetrahedron Lett. 2000, 41, 8147-8151.
34. S. N. N. Babu, G. R. Srinivasa, D. C. Santhosh, D. C. Gowda, J. Chem. Res. Synop. 2004, 66-67.
35. 2O solution (5:1), see Refs. [8,9]). The results obtained by Fujii et al. could be nicely reproduced by performing this separation under the original conditions.
36. J. R. Larrow, E. N. Jacobsen, Top. Organomet. Chem. 2004, 7, 123-152.
37. T. V. Hansen, L. Skattebøl, Tetrahedron Lett. 2005, 46, 3829-3830.
38. S. E. Schaus, B. D. Brandes, J. F. Larrow, M. Tokunage, K. B. Hansen, A. E. Gould, M. E. Furrow, E. N. Jacobsen, J. Am. Chem. Soc. 2002, 124, 1307-1315.
39. III(3)(OAc)] improved from 75.0% to 93.0 % ee when the temperature was lowered from 25°C to 10°C. Extractions run at room temperature (not thermostated) gave erratic results (83 ± 10% ee).
40. The variation of other parameters (stirring speed, concentrations, type of reaction vessel) did not significantly affect the extraction results (yields and enantioselectivities). Once the extraction was complete, the enantiomeric excesses did not vary over additional time.
41. E. V. Kudrik, S. V. Makarov, A. Zahl, R. van Eldik, Inorg. Chem. 2003, 42, 618-624.
42. II(3)] recovery process is under active investigation in our laboratories.
43. II(3)].