Copper(II)-mediated resolution of α-halo carboxylic acids with chiral O,O′-dibenzoyltartaric acid: Spontaneous racemization and crystallization-induced dynamic resolution

Organic and Biomolecular Chemistry

Volumn 3, Issue 23, 2005, Pages 4227-4232

  Xu, Hong Wu ^a,c   Wang, Qi Wei ^a   Zhu, Jin ^a,c   Deng, Jin Gen ^a,c   Cun, Lin Feng ^a   Cui, Xin ^a   Wu, Jun ^a   Xu, Xin Liang ^b   Wu, Yu Liang ^b  

^a CHENGDU INSTITUTE OF ORGANIC CHEMISTRY   (China)

^b Zhejiang Apeloa Medical Technology Co Ltd   (China)

^c UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID; CATALYST SELECTIVITY; COPPER COMPOUNDS; CRYSTALLIZATION; DECOMPOSITION; HYDRATES; MOLECULAR STRUCTURE;

CRYSTALLIZATION-INDUCED DYNAMIC RESOLUTION (CIDR); ENANTIOSELECTIVITY; RACEMIC ACIDS; RACEMIZATION;

CARBOXYLIC ACIDS;

EID: 29144509491     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b510170k     Document Type: Article

References (37)

1. J. Jaques, A. Collet, and S. H. Wilen, Enantiomers, Racemates and Resolutions, Wiley, New York, 1981.
2. For recent reports on crystallization-induced dynamic resolution (CIDR), see: J. G. Chen, J. Zhu, P. M. Skonezny, V. Rosso and J. J. Venit, Org. Lett., 2004, 6, 3233;
3. S. Kiau, R. P. Discordia, G. Madding, F. J. Okuniewicz, V. Rosso and J. J. Venit, J. Org. Chem., 2004, 69, 4256;
4. J. Košmrlj, L. O. Weigel, D. A. Evans, C. W. Downey and J. Wu, J. Am. Chem. Soc., 2003, 125, 3208;
5. H. Kaku, S. Takaoka and T. Tsunoda, Tetrahedron, 2002, 58, 3401 and references therein;
6. W. H. J. Boesten, J.-P. G. Seerden, B. de Lange, H. J. A. Dielemans, H. L. M. Elsenberg, B. Kaptein, H. M. Moody, R. M. Kellogg and Q. B. Broxterman, Org. Lett., 2001, 3, 1121;
7. W. Aelterman, Y. Lang, B. Willemsens, I. Vervest, S. Leurs and F. D. Knaep, Org. Process Res. Dev., 2001, 5, 467;
8. A. Kolarovic, D. Berkeš, P. Baran and F. Povazanec, Tetrahedron Lett., 2001, 42, 2579.
9. For related reviews on crystallization-induced dynamic resolution (CIDR), see: M. C. Millier and P. J. Reader, Drug Discovery Today, 2002, 7, 303;
10. E. J. Ebbers, G. J. A. Ariaans, J. P. M. Houbiers, A. Bruggink and B. Zwanenburg, Tetrahedron, 1997, 53, 9417;
11. S. Caddick and K. Jenkins, Chem. Soc. Rev., 1996, 447;
12. R. S. Ward, Tetrahedron: Asymmetry, 1995, 6, 1475.
13. M. Valeriano, P. Daverio, and S. Bianchi, US Pat. 6 737 411, 2004.
14. A. Badore, D. Frehel, J. P. Maffrand, and E. Vallee, US Pat. 4 740 510, 1988 (CA, 107: 89900);
15. M. Bouisset, and J. Radisson, US Pat. 5 036 156, 1991 (CA, 115: 114486).
16. O. Ko, H. Yukihiro, and K. Isao, JP Pat. 200 034 256, 2000 (CA, 132: 122386).
17. A. Mravik, Z. Böcskei, Z. Katona, I. Markovits and E. Fogassy, Angew. Chem., Int. Ed., 1997, 36, 1534.
18. A. Mravik, Z. Böcskei, Z. Katona, I. Markovits, G. Pokol, D. K. Menyhárd and E. Fogassy, Chem. Commun., 1996, 1983.
19. A. Mravik, Z. Böcskei, K. Simon, F. Elekes and Z. Izsáki, Chem. Eur. J., 1998, 4, 1621.
20. 2) C, H, N, Cu: calcd, 40.67%, 2.93%, 0, 15.4%; found, 40.54%, 3.03%, 0, 15.2%.
21. C. Dendrinou-Samara, D. P. Kessissoglou, G. E. Manoussakis, D. Mentzafos and A. Terzis, J. Chem. Soc., Dalton Trans., 1990, 959 and references therein;;
22. C. Dendrinou-Samara, P. D. Jannakoudakis, D. P. Kessissoglou, G. E. Manoussakis, D. Mentzafos and A. Terzis, J. Chem. Soc., Dalton Trans., 1992, 3259.
23. J. E. Weder, T. W. Hambely, B. J. Kennedy, P. A. Lay, D. MacLachlan, R. Bramley, C. D. Delfs, K. S. Murray, B. Moubaraki, B. Warwick, J. R. Biffin and H. L. Regtop, Inorg. Chem., 1999, 38, 1736 and references therein.
24. G. B. Deacon and R. J. Phillips, Coord. Chem. Rev., 1980, 33, 227;
25. K. Nakamoto, Infrared Spectra of Inorganic and Coordination Compounds, Wiley, New York, 1963.
26. Y. Mathey, D. R. Greig and D. F. Shriver, Inorg. Chem., 1982, 21, 3409.
27. J. Liao, X. Peng, J. Zhang, K. Yu, X. Cui, J. Zhu and J. Deng, Org. Biomol. Chem., 2003, 1080;
28. H. Tomori, H. Yoshihara and K. Ogura, Bull. Chem. Soc. Jpn., 1996, 69, 3581.
29. 1 was obtained.
30. 2]·1.5 MeCN.
31. This can be confirmed by the following experiment. The complex with 79.8% diastereomeric excess, which was obtained by filtration when the reaction had been conducted for 2 d, was suspended in acetonitrile, and stirred at 40°C for 5 d. HPLC analysis showed that the diastereomic excess was increased to 85.2%.
32. The phenomenon that different enantiomer was obtained when different solvents were used can also be observed in the coordination-mediated resolution of mandelic acid ester (see reference 8).
33. 1 (93.6% ee) was stirred in ethanol for 2 d at 40°C, HPLC analysis showed that there was only slight racemization (88.7% ee) and also no racemization was observed in ethyl acetate and toluene.
34. 1 with 87.7% ee was obtained after the treatment of the complex with HCl.
35. H. L. Haller, P. D. Bartlett, N. L. Drake, M. S. Newman, S. J. Cristol, C. M. Eaker, R. A. Hayes, G. W. Kilmer, B. Magerlein, G. P. Mueller, A. Schneider and W. Wheatley, J. Am. Chem. Soc., 1945, 67, 1591.
36. A. S. Dutta, M. B. Giles, J. J. Gormley, J. C. Williams and E. J. Kusner, J. Chem. Soc., Perkin Trans. 1, 1987, 111.
37. G. Kirchner, M. P. Scollar and A. M. Klibanov, J. Am. Chem. Soc., 1985, 107, 7072.