Nonenzymatic kinetic resolution of racemic 2,2,2-trifluoro-1-aryl ethanol via enantioselective acylation

Tetrahedron

Volumn 65, Issue 11, 2009, Pages 2232-2238

  Xu, Qing ^a   Zhou, Hui ^a   Geng, Xiaohong ^a   Chen, Peiran ^a  

^a Center for Advanced Low Dimension Materials   (China)

Author keywords

2,2,2 Trifluoro 1 aryl ethanol; Benzotetramisole; Enantioselective acylation; Nonenzymatic kinetic resolution

Indexed keywords

2,2,2 TRIFLUORO 1 ETHANOL; ALCOHOL; BENZENE DERIVATIVE; BENZOTETRAMISOLE; TETRAMISOLE; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; ENANTIOMER; ENANTIOSELECTIVITY; ENZYME KINETICS; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE;

TRIFLUORO;

EID: 59749091853     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.01.058     Document Type: Article

References (36)

1. Dolbier Jr. W.R. J. Fluorine Chem. 126 (2005) 157-163
2. Ma J.-A., and Cahard D. Chem. Rev. 104 (2004) 6119-6146
3. Chong J.M., and Mar E.K. J. Org. Chem. 56 (1991) 893-896
4. Nankamura K., Matsuda T., Shimizu M., and Fujisawa T. Tetrahedron 54 (1998) 8393-8402
5. Matsuda T., Harada T., Nakajima N., Itoh T., and Nakamura K. J. Org. Chem. 65 (2000) 157-163
6. Yong K.H., and Chong J.M. Org. Lett. 4 (2002) 4139-4142
7. Thomas C., Rosen T.C., Feldmann R., Pascal Dünkelmann P., and Daußmann T. Tetrahedron Lett. 47 (2006) 4803-4806
8. Kuroki Y., and Iseki K. Tetrahedron Lett. 40 (1999) 8231-8234
9. Chang Y., and Cai C. Tetrahedron Lett. 46 (2005) 3161-3164
10. Song J.J., Tan Z., Reeves J.T., Gallou F., Yee N.K., and Senanayake C.H. Org. Lett. 7 (2005) 2193-2196
11. Mizuta S., Shibata N., Akiti S., Fujimoto H., Nakamura S., and Toru T. Org. Lett. 9 (2007) 3707-3710
12. Zhao H., Qin B., Liu X., and Feng X. Tetrahedron 63 (2007) 6822-6826
13. Mizuta S., Shibata N., Hibino M., Nagano S., Nakamura S., and Toru T. Tetrahedron 63 (2007) 8521-8528
14. Zhu S.-F., Pang W., Xing C.-H., and Zhu S.-Z. Chin. J. Chem. 25 (2007) 233-236
15. Lin J.T., Yamazaki T., and Kitazume T. J. Org. Chem. 52 (1987) 3211-3217
16. Gaspar J., and Guerrero A. Tetrahedron: Asymmetry 6 (1995) 231-238
17. Kato K., Katayama M., Gautam R.K., Fujii S., and Kimoto H. J. Biosci. Biotechnol. Biochem. 59 (1995) 271-276
18. Kato K., Katayama M., Fujii S., Fukaya H., and Kimoto H. J. Ferment. Bioeng. 81 (1996) 206-211
19. Kato K., Gong Y.-F., Tanaka S., Katayama M., and Kimoto H. J. Mol. Catal. B: Enzym. 11 (2001) 287-294
20. Kourist R., Krishna S.H., Patel J.S., Bartnek F., Hitchman T.S., David P., Weiner D.P., and Bornscheuer U.T. Org. Biomol. Chem. 5 (2007) 3310-3313
21. For review, see:. Vedejs E., and Jure M. Angew. Chem., Int. Ed. 44 (2005) 3974-4001 For original articles, see:
22. Oriyama T., Hori Y., lmai K., and Sasaki R. Tetrahedron Lett. 37 (1996) 8543-8546
23. Ruble J.C., Latham H.A., and Fu G.C. J. Am. Chem. Soc. 119 (1997) 1492-1493
24. Kawabata T., Nagato M., Takasu K., and Fuji K. J. Am. Chem. Soc. 119 (1997) 3169-3170
25. Garrett C.E., and Fu G.C. J. Am. Chem. Soc. 120 (1998) 7479-7483
26. Ruble J.C., Tweddell J., and Fu G.C. J. Org. Chem. 63 (1998) 2794-2795
27. Tao B., Ruble J.C., Hoic D.A., and Fu G.C. J. Am. Chem. Soc. 121 (1999) 5091-5092
28. Jarvo E.R., Copeland G.T., Papaioannou N., Bonitatebus Jr. P.J., and Miller S.J. J. Am. Chem. Soc. 121 (1999) 11638-11643
29. Edwin Vedejs E., and MacKay J.A. Org. Lett. 3 (2001) 535-536
30. Birman V.B., and Jiang H. Org. Lett. 7 (2005) 3445-3447
31. Birman V.B., and Li X. Org. Lett. 8 (2006) 1351-1359
32. Vladimir B., Birman V.B., Li X., Jiang H., and Uffman E.W. Tetrahedron 62 (2006) 285-294
33. Birman V.B., and Guo L. Org. Lett. 8 (2006) 4859-4861
34. Zhou H., Xu Q., and Chen P. Tetrahedron 64 (2008) 6494-6499
35. Kagan H.B., and Fiaud J.C. In: Eliel E.L., and Wilen S.H. (Eds). Topics in Stereochemistry Vol. 18 (1988), John Wiley and Sons, New York, NY 249-330
36. Data taken from. In: March J. (Ed). Advanced Organic Chemistry (1992), John Wiley & Sons, New York, NY 15