Improvement of the asymmetry-inducing ability of a trifluoromethylated amino alcohol by electron donation to a CF3 group

Tetrahedron Asymmetry

Volumn 19, Issue 10, 2008, Pages 1210-1214

  Harada, Akinori ^a   Fujiwara, Yasuyuki ^a   Katagiri, Toshimasa ^a  

^a OKAYAMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMINOALCOHOL;

ALKYLATION; ARTICLE; CHEMICAL STRUCTURE; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; METHYLATION; PRIORITY JOURNAL; PURIFICATION; SUBSTITUTION REACTION;

EID: 44649155005     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2008.04.023     Document Type: Article

References (40)

1. Uneyama K. Organofluorine Chemistry (2006), Blackwell, Oxford Chapter 5
2. Kubota T. In: Soloshonok V.A. (Ed). Enantiocontrolled Synthesis of Fluoro-organic Compounds (1999), Wiley, Chichester Chapter 15
3. Fache F. New. J. Chem. 28 (2004) 1277
4. Doyle A.G., and Jacobsen E.N. Chem. Rev. 107 (2007) 5713
5. Mallat T., Orgimaister E., and Baiker A. Chem. Rev. 107 (2007) 4863
6. Horvath I.T., and Rabai J. Science 266 (1994) 72
7. Gladysz J.A., and Curran D.P. Tetrahedron 58 (2000) 3823 (Introduction of Tetrahedron Symposium-In-Print)
8. Hashimoto T., and Maruoka K. Chem. Rev. 107 (2007) 5656
9. Nagai T., Nishioka G., Koyama M., Ando A., Miki T., and Kumadaki I. J. Fluorine Chem. 57 (1992) 229
10. Katagiri T., Yamaji S., Handa M., Irie M., and Uneyama K. Chem. Commun. (2001) 2054
11. Crampton M.R., Emokpae T.A., and Isanbor C. Eur. J. Org. Chem. (2007) 1378
12. Della E.W. J. Am. Chem. Soc. 89 (1967) 5221
13. Charton M. J. Am. Chem. Soc. 97 (1975) 1552
14. Kitching W., Olszowy H.A., and Drew G.M. J. Org. Chem. 47 (1982) 5153
15. Nagai T., Nishioka G., Koyama M., Ando A., Miki T., and Kumadaki I. J. Fluorine Chem. 57 (1992) 229
16. Schlosser M., and Michel D. Tetrahedron 52 (1996) 99
17. Katagiri T., and Uneyama K. J. Fluorine Chem. 105 (2000) 285
18. Itoh Y., Yamanaka M., and Mikami K. Org. Lett. 5 (2003) 4803
19. Itoh Y., Yamanaka M., and Mikami K. Org. Lett. 5 (2003) 4807
20. Katagiri T., and Uneyama K. Chirality 15 (2003) 4
21. Mikami K., Itoh Y., and Yamanaka M. Chem. Rev. 104 (2004) 1
22. Bzhezovskii V.M., Chura M.B., and Il'chenko N.N. Russ. J. Gen. Chem. 76 (2006) 359
23. Carcenac Y., Diter P., Wakselman C., and Tordeux M. New. J. Chem. 30 (2006) 442
24. Uneyama K. Organofluorine Chemistry (2006), Blackwell, Oxford Chapter 1
25. Taft R.W. In: Newman M.S. (Ed). Steric Effects in Organic Chemistry (1956), Wiley, New York, NY 556
26. sBu molecules respectively estimated by PM3 level MO calculation (MacSpartan Pro).
27. Katagiri T., Fujiwara Y., Takahashi S., Ozaki N., and Uneyama K. Chem. Commun. (2002) 986-987
28. Fujiwara Y., Katagiri T., and Uneyama K. Tetrahedron Lett. 44 (2003) 6161
29. Katagiri T., Iguchi N., Kawate T., Takahashi S., and Uneyama K. Tetrahedron: Asymmetry 17 (2006) 1157
30. Katagiri T., Yamaji S., Handa M., Irie M., and Uneyama K. Chem. Commun. (2001) 2054
31. Noyori R. Asymmetric Catalysis in Organic Synthesis (1994), John Wiley & Sons, New York pp. 265
32. McBee E.T., Hathaway C.E., and Roberts C.W. J. Am. Chem. Soc. 78 (1956) 3851
33. Katagiri T. In: Soloshonok V.A. (Ed). Enantiocontrolled Synthesis of Fluoro-organic Compounds: Stereochemical Challenges and Biomedical Targets (1999), John Wiley and Sons, New York 161
34. Katagiri T., Takahashi M., Fujiwara Y., Ihara H., and Uneyama K. J. Org. Chem. 64 (1999) 7323
35. Schaus S.E., Brandes B.D., Larrow J.F., Tokunaga M., Hansen K.B., Gould A.E., Furrow M.E., and Jacobsen E.N. J. Am. Chem. Soc. 124 (2002) 1307
36. Yamauchi Y., Katagiri T., and Uneyama K. Org. Lett. 4 (2002) 173
37. Yamauchi Y., Kawate T., Katagiri T., and Uneyama K. Tetrahedron 59 (2003) 9839
38. Preparations and purifications of the non-fluorinated aminoalcohols, see:. Koppenhoefer B., and Schurig V. Org. Synth. 66 (1988) 151
39. Koppenhoefer B., and Schurig V. Org. Synth. 66 (1988) 160
40. Douglas J.A., Stefano C., and Charles J.M.S. J. Chem. Soc., Perkin Trans. 1 (1976) 492