Dynamic kinetic resolution of α-chloro esters in asymmetric nucleophilic substitution using diacetone-D-glucose as a chiral auxiliary

Tetrahedron Letters

Volumn 46, Issue 23, 2005, Pages 4115-4117

  Hyun, Jung Kim ^a   Shin, Eun Kyoung ^a   Chang, Ji Yeon ^a   Kim, Yongtae ^a   Yong, Sun Park ^a  

^a Konkuk University   (South Korea)

Author keywords

Asymmetric syntheses; Carbohydrate; Chiral auxiliary; Dynamic kinetic resolution; Nucleophilic substitution

Indexed keywords

ACETONYLACETONE; AMINE; AMINO ACID; ESTER DERIVATIVE; GLUCOSE;

ARTICLE; CHEMICAL REACTION; CHIRALITY; KINETICS; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SUBSTITUTION REACTION; SYNTHESIS;

EID: 18944373681     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.04.003     Document Type: Article

References (31)

1. For reviews on dynamic resolution of α-halo esters, see: Y. Valenrod, J. Myung, and R.N. Ben Tetrahedron Lett. 45 2004 2545
2. J. Nam, S.-k. Lee, and Y.S. Park Tetrahedron 59 2003 2397
3. J. Nam, S.-k. Lee, K.Y. Kim, and Y.S. Park Tetrahedron Lett. 43 2002 8253
4. S.-k. Lee, J. Nam, and Y.S. Park Synlett 2002 790
5. R.N. Ben, and T. Durst J. Org. Chem. 64 1999 7700
6. For reviews on dynamic resolution of α-halo amides, see: J.-y. Chang, E.-k. Shin, H.J. Kim, Y. Kim, and Y.S. Park Tetrahedron 61 2005 2743
7. J. Nam, J.-y. Chang, E.-k. Shin, H.J. Kim, Y. Kim, S. Jang, and Y.S. Park Tetrahedron 60 2004 6311
8. J. Nam, J.-y. Chang, K.-S. Hahm, and Y.S. Park Tetrahedron Lett. 44 2003 7727
9. S. Caddick, C.A.M. Afonso, S.X. Candeias, P.B. Hitchcock, K. Jenkins, L. Murtagh, D. Pardoe, A.G. Santos, N.R. Treweeke, and R. Weaving Tetrahedron 57 2001 6589
10. S.-k Lee, S.Y. Lee, and Y.S. Park Synlett 2001 1941
11. A. Kubo, H. Kubota, M. Takahashi, and K. Nunami J. Org. Chem. 62 1997 5830
12. R.S. Ward, A. Pelter, D. Goubet, and M.C. Pritchard Tetrahedron: Asymmetry 6 1995 469
13. L.-L. Huang, M.-H. Xu, and G.-Q. Lin J. Org. Chem. 70 2005 529
14. S. Knauer, and H. Kunz Tetrahedron: Asymmetry 16 2005 529
15. C.W.Y. Chung, and P.H. Toy Tetrahedron: Asymmetry 15 2004 387
16. K. Totani, K. Takao, and K. Tadano Synlett 2004 2066
17. F. Chéry, M. Desroses, A. Tatibouët, O.D. Lucchi, and P. Rollin Tetrahedron 59 2003 4563
18. H. Yu, C.E. Ballard, P.D. Boyle, and B. Wang Tetrahedron 58 2002 7663
19. E.J. Enholm, J.S. Cottone, and F. Allais Org. Lett. 3 2001 145
20. K. Totani, T. Nagatsuka, S. Yamaguchi, and K. Takao J. Org. Chem. 66 2001 5965
21. T. Bach, and F. Höfer J. Org. Chem. 66 2001 3427
22. N. Khiar, F. Alcudia, J.-L. Espartero, L. Rodriguez, and I. Fernández J. Am. Chem. Soc. 122 2000 7598
23. G. Huang, and R.I. Hollingsworth Tetrahedron Lett. 40 1999 581
24. T. Yoshida, J. Chika, and H. Takei Tetrahedron Lett. 39 1998 4305
25. P. Hultin, M.A. Earle, and M. Sudharshan Tetrahedron 53 1997 14823
26. C. Chiappe, G.L. Moro, and P. Munforte Tetrahedron: Asymmetry 8 1997 2311
27. P. Angibaud, J.L. Chaumette, J.R. Desmurs, L. Duhamel, G. Plé, J.Y. Valnot, and P. Duhamel Tetrahedron: Asymmetry 6 1995 1919
28. 3N gave a substitution product with low diastereoselectivity (2:1)
29. The absolute configurations of (αS)-2 and (αS)-6 were determined after the removal of chiral auxiliary by comparison of the CSP-HPLC retention time with authentic products prepared from L-phenylglycine
30. 7 The enantiomeric ratio of 17 was determined to be 96:4 in favor of the S-enantiomer by CSP-HPLC using racemic material as a standard (Chiralcel OD column; 10% 2-propanol in hexane; 0.5 mL/min; The S-enantiomer (major) had a retention time of 18.6 min, and the R-enantiomer (minor) had a retention time of 17.7 min.)
31. Y.S. Park, and P. Beak J. Org. Chem. 62 1997 1574