Kinetic resolution of 2-oxazolidinones via catalytic, enantioselective N-acylation

Journal of the American Chemical Society

Volumn 128, Issue 20, 2006, Pages 6536-6537

  Birman, Vladimir B ^a   Jiang, Hui ^a   Li, Ximin ^a   Guo, Lei ^a   Uffman, Eric W ^a  

^a WASHINGTON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 OXAZOLIDINONE DERIVATIVE; CYTOXAZONE; FURAN DERIVATIVE; THIOPHENE DERIVATIVE; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CONCENTRATION (PARAMETERS); ENANTIOSELECTIVITY; KINETICS; SYNTHESIS;

ACYLATION; AMIDES; KINETICS; OXAZOLIDINONES; STEREOISOMERISM;

EID: 33646737239     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja061560m     Document Type: Article

References (31)

1. Kagan, H. B.; Fiaud, J. C. Top. Stereochem. 1988, 18, 249.
2. Enzymatic enantioselective acylation of alcohols: (a) Sih, C. J.; Wu, S.-H. Top. Stereochem. 1989, 19, 63.
3. (b) Klibanov, A. M. Acc. Chem. Res. 1990, 23, 114.
4. (c) Schoffers, E.; Golebiowski, A.; Johnson, C. R. Tetrahedron 1996, 52, 3769.
5. Enzymatic enantioselective acylation of amines: van Rantwijk, F.; Sheldon, R. A. Tetrahedron 2004, 60, 501.
6. For recent reviews, see: (a) Vedejs, E.; Jure, M. Angew. Chem., Int. Ed. 2005, 44, 3974.
7. (b) Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2004, 43, 5138.
8. (c) Jarvo, E. R.; Miller, S. J. Asymmetric Acylation. In Comprehensive Asymmetric Catalysis, Supplement I: Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Berlin, Heidelberg, 2004; Chapter 43.
9. (d) France, S.; Guerin, D. J.; Miller, S. J.; Lectka, T. Chem. Rev. 2003, 103, 2985.
10. Arai, S.; Bellemin-Laponnaz, S.; Fu, G. C. Angew. Chem., Int. Ed. 2001, 40, 234.
11. Resolution of chiral oxazolidinones has been achieved by (a) chromatographic separation of their diastereomeric N-acyl derivatives: Ishizuka, T.; Kimura, K.; Ishibuchi, S.; Kunieda, T. Chem. Lett. 1992, 991; and
12. (b) enantioselective deacylation of N-acyl-oxazolidinones via catalytic, asymmetric borane reduction: Hashimoto, N.; Ishizuka, T.; Kunieda, T. Tetrahedron Lett. 1998, 39, 6317.
13. (a) Kano, S.; Yokomatsu, T.; Shibuya, S. Heterocycles 1990, 31, 1711.
14. (b) Ager, D. J.; Allen, D. R.; Schaad, D. R. Synthesis 1996, 1283.
15. (a) Flynn, D. L.; Zelle, R. E.; Grieco, P. A. J. Org. Chem. 1983, 48, 2424.
16. (b) Grehn, L.; Ragnarsson, U. Angew. Chem., Int. Ed. Engl. 1985, 24, 510.
17. (c) Hansen, M. M.; Harkness, A. R.; Coffey, D. S.; Bordwell, F. G.; Zhao, Y. Tetrahedron Lett. 1995, 36, 8949.
18. (a) Birman, V. B.; Uffman, E. W.; Jiang, H.; Li, X.; Kilbane, C. J. J. Am. Chem. Soc. 2004, 126, 12226.
19. (b) Birman, V. B.; Jiang, H. Org. Lett. 2005, 7, 3445.
20. (c) Birman, V. B.; Li, X.; Jiang, H.; Uffman, E. W. Tetrahedron 2006, 62, 285.
21. (d) Birman, V. B.; Li, X. Org. Lett. 2006, 8, 1351.
22. Selectivity Factor is defined as s = k(fast-reacting enantiomer)/k(slow- reacting enantiomer). Both % conversion and selectivity factor are calculated from ee's of the product and the recovered starting material.1 Average values of duplicate runs are given for the % ee, % C and s.
23. Ruble, J. C.; Tweddell, J.; Fu, G. C. J. Org. Chem. 1998, 63, 2794.
24. Gradual dissolution of a racemic substrate in the course of KR will lead to a lower apparent selectivity compared with that in a homogeneous reaction.
25. Hamersak, Z.; Ljubovic, E.; Mercep, M.; Mesic, M.; Sunjic, V. Synthesis 2001, 1989. In the original synthetic route, (-)-cytoxazone 6d was obtained by KR of its racemate via enzymatic O-acylation with s = 39.
26. Isolation, structure elucidation, and biological activity: (a) Kakeya, H.; Morishita, M.; Kobinata, K.; Osono, M.; Ishizuka, M.; Osada, H. J. Antibiol. 1998, 51, 1126.
27. (b) Kakeya, H.; Morishita, M.; Koshino, H.; Morita, T.-i.; Kobayashi, K.; Osada, H. J. Org. Chem. 1999, 64, 1052.
28. For a list of leading references to synthesis of 6d, see: (c) Kim, J. D.; Kim, I. S.; Jin, C. H.; Zee, O. P.; Jung, Y. H. Org. Lett. 2005, 7, 4025.
29. HPLC = 45%, s = 56) and 79% recovered catalyst.
30. 2) and 60% recovered catalyst.
31. HPLC = 52%, s = 94) and 62% recovered catalyst. See experimental details in Supporting Information.