Concise access to enantiopure (S)- and (R)-α-trifluoromethyl pyroglutamic acids from ethyl trifluoropyruvate-based chiral CF3-oxazolidines (Fox)

Journal of Fluorine Chemistry

Volumn 129, Issue 11, 2008, Pages 1104-1109

  Chaume, Grégory ^a   Van Severen, Marie Céline ^a   Ricard, Louis ^b   Brigaud, Thierry ^a  

^a Université Paris Seine   (France)

^b LABORATOIRE HÉTÉROÉLÉMENTS ET COORDINATION   (France)

Author keywords

Trifluoromethyl amino acids; Lactams; Organofluorine chemistry; Oxazolidines; Ring closure; Stereoselective synthesis

Indexed keywords

EID: 53649111432     PISSN: 00221139     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jfluchem.2008.07.019     Document Type: Article

References (45)

1. For recent entries, see:
2. Mikhailiuk P.K., Afonin S., Chernega A.N., Rusanov E.B., Platonov M.O., Dubinina G.G., Berditsch M., Ulrich A.S., and Komarov I.V. Angew. Chem. Int. Ed. 45 (2006) 5659-5661
3. van Esseveldt B.C.J., Vervoort P.W.H., van Delft F.L., and Rutjes F.P.J.T. J. Org. Chem. 70 (2005) 1791-1795 (and references therein)
4. Jenkins C.L., Lin G., Duo J., Rapolu D., Guzei I.A., Raines R.T., and Krow G.R. J. Org. Chem. 69 (2004) 8565-8573 (and references therein)
5. Karoyan P., Sagan S., Lequin O., Quancard J., Lavielle S., and Chassaing G. Targets Heterocycl. Syst. 8 (2004) 216-273
6. Del Valle J.R., and Goodman M. J. Org. Chem. 68 (2003) 3921-3933 (and references therein)
7. Zhang J., Wang W., Xiong C., and Hruby V.J. Tetrahedron Lett. 44 (2003) 1413-1415
8. Moroder L., Renner C., Lopez J.J., Mutter M., and Tuchscherer G. In: Dugave C. (Ed). Cis-trans Isomerization in Biochemistry (2006), Wiley-VCH, Weinheim, Germany
9. Flores-Ortega A., Jiménez A.I., Cativiela C., Nussinov C., Aleman R., and Casanovas J. J. Org. Chem. 73 (2008) 3418-3427 (and references therein)
10. Dugave C., and Demange L. Chem. Rev. 103 (2003) 2475-2532
11. Kitamoto T., Ozawa T., Abe M., Marubayashi S., and Yamazaki T. J. Fluorine Chem. 129 (2008) 286-293
12. Guo Y., Fujiwara K., Amii H., and Uneyama K. J. Org. Chem. 72 (2007) 8523-8526 (and references therein)
13. Lange U.E.W., Baucke D., Hornberger W., Mack H., Seitz W., and Höffken H.W. Bioorg. Med. Chem. Lett. 16 (2006) 2648-2653
14. Kim W., McMillan R.A., Snyder J.P., and Conticello V.P. J. Am. Chem. Soc. 127 (2005) 18121-18132
15. Kim W., Hardcastle K.I., and Conticello V.P. Angew. Chem. Int. Ed. 45 (2006) 8141-8145
16. Kukhar V.P., and Soloshonok V.A. Fluorine Containing Amino Acids, Synthesis and Properties (1995), Wiley,, New York (and references cited therein)
17. Qui X.-L., Meng W.-D., and Qing F.-L. Tetrahedron 60 (2004) 6711-6745
18. Molteni M., Pesenti C., Sani M., Volonterio A., and Zanda M. J. Fluorine Chem. 125 (2004) 1735-1743
19. Luppi G., Lanci D., Trigari V., Garavelli M., Garelli A., and Tomasini C. J. Org. Chem. 68 (2003) 1982-1993 (and references therein)
20. Tomasini C., and Villa M. Tetrahedron Lett. 42 (2001) 5211-5214
21. For literature concerning fluorinated pyroglutamic acids, see:
22. Qing F.-L., and Qiu X.-L. Synthesis of fluorinated prolines and pyroglutamic acids. In: Soloshonok V.A. (Ed). Fluorine Containing Synthons (2005), American Chemical Society, Washington, DC 562 (and references therein)
23. Qiu X.-L., Meng W.-D., and Qing F.-L. Tetrahedron 60 (2004) 5201-5206
24. Qiu X.-L., Meng W.-D., and Qing F.-L. J. Org. Chem. 68 (2003) 3614-3617
25. Soloshonok V.A., Cai C., Hruby V.J., Van Meervelt L., and Mischenko N. Tetrahedron 55 (1999) 12031-12044
26. Soloshonok V.A., Cai C., Hruby V.J., and Van Meervelt L. Tetrahedron 55 (1999) 12045-12058
27. Soloshonok V.A., Avilov D.V., Kukhar V.P., Van Meervelt L., and Mischenko N. Tetrahedron Lett. 38 (1997) 4903-4904
28. Gestmann D., Laurent A.J., and Laurent E.G. J. Fluorine Chem. 80 (1996) 27-30
29. α-Tfm-pyroglutamic acid has only been reported in the racemic series:
30. Koksch B., Ullmann D., Jakubke H.-D., and Burger K. J. Fluorine Chem. 80 (1996) 53-57
31. Huguenot F., and Brigaud T. J. Org. Chem. 71 (2006) 7075-7078
32. Huguenot F., and Brigaud T. J. Org. Chem. 71 (2006) 2159-2162
33. Lebouvier N., Laroche C., Huguenot F., and Brigaud T. Tetrahedron Lett. 43 (2002) 2827-2830
34. Brigaud T., Chaume G., Pytkowicz J., and Huguenot F. Chim. Oggi Chem. Today 25 (2007) 8-10
35. Chaume G., Van severen M.-C., Marinkovic S., and Brigaud T. Org. Lett. 8 (2006) 6123-6126
36. The formation of similar oxazolidines has already been reported in the non-fluorinated series:
37. Agami C., Couty F., Prince B., and Venier O. Tetrahedron Lett. 37 (1993) 7061-7062
38. Harwood L.M., Vines K.J., and Drew M.G.B. Synlett (1996) 1051-1053
39. In our previous report (Ref. 9) we observed that the chromatographic separation of both diastereomers of similar bicyclic CF3-morpholinones was very easy.
40. The synthesis of similar bicyclic lactams has also been reported in the non fluorinated series by an alternative strategy:
41. Harwood L.M., Hamblett G., Jimenez-Dias A.I., and Watkin D.J. Synlett (1997) 935-938
42. f of (R,S)-7 = 0.41 (7:3 cyclohexane/ethyl acetate) and Rf of (R,R)-7 = 0.29 (7:3 cyclohexane/ethyl acetate).
43. Crystallographic data (excluding structure factors) for compound (R,S)-7 have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC 695212. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: + 44 1223 336033 or email: deposit@ccdc.cam.ac.uk.
44. Tang G., Tian H., and Ma D. Tetrahedron 60 (2004) 10547-10552
45. Ma D., Tang G., Tian H., and Zou G. Tetrahedron Lett. 40 (1999) 5753-5756