Enantioselective aminolytic kinetic resolution (AKR) of epoxides catalyzed by recyclable polymeric Cr(III) salen complexes

Tetrahedron Asymmetry

Volumn 17, Issue 11, 2006, Pages 1638-1643

  Kureshy, Rukhsana I ^a   Singh, Surendra ^a   Khan, Noor ul H ^a   Abdi, Sayed H R ^a   Agrawal, Santosh ^a   Jasra, Raksh V ^a  

^a CSIR CENTRAL SALT AND MARINE CHEMICALS RESEARCH INSTITUTE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

CHROMIUM; EPOXIDE; POLYMER; SODIUM CHLORIDE;

AMINOLYSIS; ARTICLE; CATALYSIS; CHIRALITY; ENANTIOSELECTIVITY; EPOXIDATION; KINETICS; PRIORITY JOURNAL; ROOM TEMPERATURE;

EID: 33745851859     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2006.05.029     Document Type: Article

References (40)

1. Jacobsen E.N., and Wu M.H. In: Jacobsen E.N., Pflaz A., and Yamamoto H. (Eds). Ring Opening of Epoxides and Related Reactions in Comprehensive Asymmetric Catalysis Vol. III (1999), Springer-Verlag, Berlin 1309
2. Hodgson D.M., Gibbs A.R., and Lee G.P. Tetrahedron 52 (1996) 14361
3. Bergmeier S.C. Tetrahedron 56 (2000) 2561
4. Ager D.J., Prakash I., and Schaad D.R. Chem. Rev. 96 (1996) 835
5. Li G., Chang H.-T., and Sharpless K.B. Angew. Chem., Int. Ed. 35 (1996) 451
6. Review:. O'Brien P. Angew. Chem., Int. Ed. 38 (1999) 326
7. List B. J. Am. Chem. Soc. 122 (2000) 9336
8. Córdova A., Notz W., Zhong G., Betancort J.M., and Barbas C.F. J. Am. Chem. Soc. 124 (2002) 1842
9. Trost B.M., and Terrell L.R. J. Am. Chem. Soc. 125 (2003) 338
10. Fu X.L., and Wu S.H. Synth. Commun. 27 (1997) 1677
11. Hou X.L., Wu J., Dai L.X., Xia L.J., and Tang M.H. Tetrahedron: Asymmetry 9 (1998) 1747
12. Sagawa S., Abe H., Hase Y., and Inaba T. J. Org. Chem. 64 (1999) 4962
13. Sekaine A., Ohshima T., and Shibasaki M. Tetrahedron 58 (2002) 75
14. Carrée F., Gil R., and Collin J. Tetrahedron Lett. 45 (2004) 7749
15. Carrée F., Gil R., and Collin J. Org. Lett. 7 (2005) 1023
16. Schneider C., Sreekanth A.R., and Mai E. Angew. Chem., Int. Ed. 43 (2004) 5691
17. Kureshy R.I., Singh S., Khan N.H., Abdi S.H.R., Suresh E., and Jasra R.V. Eur. J. Org. Chem. (2006) 1303
18. Kobayashi S., Hishitani H., and Ueno M. J. Am. Chem. Soc. 120 (1998) 431
19. Matsunaga S., Kumagai N., Harada S., and Shibasaki M. J. Am. Chem. Soc. 125 (2003) 4712
20. Keith J.M., Larrow J.F., and Jacobsen E.N. Adv. Synth. Catal. 343 (2002) 5
21. Label H., and Jacobsen E.N. Tetrahedron Lett. 40 (1999) 7303
22. Bandani M., Cozzi P.G., Melchiorre P., and Umani-Ronchi A. Angew. Chem., Int. Ed. 43 (2004) 84
23. Bartoli G., Bosco M., Carlone A., Locatelli M., Massaccesi M., Melchiorre P., and Sambri L. Org. Lett. 6 (2004) 2173
24. Song C.E., and Lee S. Chem. Rev. 102 (2002) 3495
25. Xia Q.-H., Ge H.-Q., Ye C.-P., Liu Z.-M., and Su K.-X. Chem. Rev. 105 (2005) 1603
26. Pugin B., and Blaser H.U. In: Jacobsen E.N., Pflaz A., and Yamamoto H. (Eds). Catalyst Immobilization: Solid Support in Comprehensive Asymmetric Catalysis III (1999), Springer, Berlin 1367
27. Oehme G. In: Jacobsen E.N., Pflaz A., and Yamamoto H. (Eds). Catalyst Immobilization: Two-Phase System in Comprehensive Asymmetric Catalysis III (1999), Springer, Berlin 1377
28. Song C.E., Oh C.R., Roh E.J., and Choo D.J. Chem. Commun. (2000) 1743
29. Kureshy R.I., Khan N.H., Abdi S.H.R., Patel S.T., and Jasra R.V. J. Mol. Catal. 179 (2002) 73
30. Kureshy R.I., Khan N.H., Abdi S.H.R., Singh S., Ahmad I., Jasra R.V., and Vyas A.P. J. Catal. 224 (2004) 229
31. Kureshy R.I., Khan N.H., Abdi S.H.R., Singh S., Ahmad I., and Jasra R.V. J. Mol. Catal. 218 (2004) 141
32. Yao X., Chen H., Lü W., Pan G., Hu X., and Zheng Z. Tetrahedron Lett. 41 (2000) 10267
33. Daly A.M., Renehan M.F., and Gilheny D.G. Org. Lett. 3 (2001) 663
34. The conversion of the product was determined on a Chiralpak OD column using calibration of peak area % of the amino alcohol and trans-stilbene oxide at 243 Lemeda Max.
35. Keck G.E., and Truong A.P. Org. Lett. 4 (2002) 3131
36. Kronenthal D.R., Han C.Y., and Taylor M.K. J. Org. Chem. 47 (1982) 2765
37. Lee N.H., Muci A.R., and Jacobsen E.N. Tetrahedron Lett. 32 (1991) 5055
38. Perrin D.D., Armarego W.L.F., and Perrin D.R. Purification of Laboratory Chemicals (1981), Pergamon, New York
39. Moyna G., Williams H.J., and Scott A.L. Synth. Commun. 26 (1996) 2235
40. Martinez L.E., Leighton J.L., Carsren D.H., and Jacobsen E.N. J. Am. Chem. Soc. 117 (1995) 5897