Asymmetric synthesis of 2-trifluoromethyl-1,2,3-triols

European Journal of Organic Chemistry

Volumn , Issue 7, 2007, Pages 1085-1090

  Enders, Dieter ^a   Herriger, Cornelia ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

Asymmetric synthesis; Nucleophilic addition; Ruppert reagent; Trifluoromethylation

Indexed keywords

EID: 34247122105     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200600895     Document Type: Article

References (41)

1. a) P. Kirsch, Modern Fluoroorganic Chemistry - Synthesis Reactivity. Applications, Wiley-VCH, Weinheim, 2004;
2. b) R. D. Chambers, Fluorine in Organic Chemistry, Blackwell Publishing Ltd., Oxford, 2004;
3. c) T. Hiyama, Organofluorine Compounds, Chemistry and Applications, Springer, Berlin, 2000.
4. J.-A. Ma, D. Cahard, Chem. Rev. 2004, 104, 6119-6146.
5. a) A. Abouabdellah, J. P. Bégué, D. Bonnet-Delpon, J. C. Gantier, N. Truong Thi Thanh, T. Truong Dinh, Bioorg. Med. Chem. Lett. 1996, 6, 2717-2720;
6. b) N. Truong Thi Thanh, C. Ménage, J. P. Bégué, D. Bonnet-Delpon, J. C. Gantier, B. Pradines, J.-C. Doury. T. Truong Dinh, J. Med. Chem. 1998, 41, 4101-4108:
7. c) F. Grellepois, F. Chorki, B. Crousse, M. Ourévitch, D. Bonnet-Delpon, J.-P. Bégué, J. Org. Chem. 2002, 67, 1253-1260.
8. Reviews on trifluoromethylation reactions: a) M. A. McClinton, D. A. McClinton. Tetrahedron 1992, 48, 6555-6666:
9. b) B. R. Langlois, T. Billard, Synthesis 2003, 185-194.
10. I. Ruppert, K. Schlich, W. Volbach, Tetrahedron Lett. 1984, 25, 2195-2198.
11. a) G. K. S. Prakash, R. Krishnamurti, G. A. Olah, J. Am. Chem. Soc 1989, 111, 393-395;
12. b) R. Krishnamurti, D. R. Bellew, G. K. S. Prakash, J. Org. Chem. 1991, 56, 984-989.
13. 3: a) G. K. S. Prakash, A. K. Yudin, Chem. Rev. 1997, 97, 757-786;
14. b) R. P. Singh, J. M. Shreeve, Tetrahedron 2000, 56, 7613-7632;
15. c) G. K. S. Prakash, M. Mandal, J. Fluorine Chem. 2001, 112, 123-131.
16. a) C. F. Morelli, G. Speranza, L. Duri, P. Manitto, Org. Prep. Proced. Int. 2002, 34, 103-107;
17. b) G. K. S. Prakash, M. Mandal, G. A. Olah, Angew. Chem. 2001, 113, 609-610;
18. Angew. Chem. Int. Ed. 2001, 40, 589-590;
19. c) G. K. S. Prakash, M. Mandal, J. Am. Chem. Soc. 2002, 124, 6538 6539;
20. d) Y. Kawano, T. Mukaiyama, Chem. Lett. 2005, 34, 894-895;
21. e) U. Eilitz, C. Böttcher, L. Hennig, K. Burger, A. Haas, S. Gockel, J. Sieler, J. Heterocycl. Chem. 2003, 40, 329-335;
22. f) S. Lavaire, R. Plantier-Royon, C. Portella, Tetrahedron: Asymmetry 1998, 9, 213-226;
23. g) C. R. Johnson. D. R. Bhumralkar, E. De Clerq, Nucleosides Nucleotides 1995, 14, 185-194:
24. h) J. Kozak, C. R. Johnson, Nucleosides Nucleotides 1998, 17, 2221-2239.
25. a) Y. Kuroki, K. Iseki, Tetrahedron Lett. 1999, 40, 8231-8234;
26. b) S. Caron, N. M. Do, P. Arpin, A. Larivée, Synthesis 2003, 1693-1698;
27. c) K. Iseki, T. Nagai, Y. Kobayashi, Tetrahedron Lett. 1994, 35, 3137-3138:
28. d) S. Roussel, T. Billard, B. R. Langlois, L. Saint-James, Chem. Eur. J. 2005, 11, 939-944.
29. a) D. Hoppe, H. Schmincke, H.-W. Kleemann, Tetrahedron 1989, 45, 687-694;
30. b) H. Vorbrüggen, Acta Chem. Scand. 1982, 420.
31. D. Enders, B. Bockstiegel, Synthesis 1989, 493-496.
32. a) D. Enders, M. Voith, Synthesis 2002, 1571-1577;
33. b) D. Enders, M. Voith, S. J. Ince, Synthesis 2002, 1775-1779.
34. For reviews see: a) D. Enders, M. Voith, A. Lenzen, Angew. Chem. 2005, 117, 1330-1351;
35. Angew. Chem. Int. Ed. 2005, 44, 1304-1325;
36. b) A. Job, C. F. Janeck, W. Bettray, R. Peters, D. Enders, Tetrahedron 2002, 58, 2253-2329 and lit. cited therein.
37. D. Enders, A. Hieronymi, A. Ridder, Synlett 2005, 2391-2393.
38. M. Majewski, P. Nowak, Tetrahedron: Asymmetry 1998, 9, 2611-2617.
39. D. Enders, A. Nühring, J. Runsink, G. Raabe, Synthesis 2001, 1406-1414.
40. a) D. Enders, P. Fey, H. Kipphardt, Org. Synth. 1987, 65, 173-182;
41. b) D. Enders, P. Fey, H. Kipphardt, Org. Synth. 1987, 65, 183-202.