One-pot synthesis of functionalized 3-(trifluoromethyl)phenols by [3+3] cyclization of 1,3-bis(silyl enol ethers) with α,β-unsaturated trifluoromethyl ketones

European Journal of Organic Chemistry

Volumn , Issue 3, 2008, Pages 492-502

  Mamat, Constantin ^a   Pundt, Thomas ^a   Dang, T H Tam ^a   Klassen, Renske ^a   Reinke, Helmut ^a   Köckerling, Martin ^a   Langer, Peter ^a  

^a UNIVERSITY OF ROSTOCK   (Germany)

Author keywords

Arenes; Cyclizations; Organic fluoro compounds; Regioselectivity; Silyl enol ethers

Indexed keywords

EID: 38949177766     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200700801     Document Type: Article

References (63)

1. a) Fluorine in Bioorganic Chemistry (Eds.: R. Filler, Y. Kobayasi, L. M. Yagupolskii), Elsevier, Amsterdam, 1993;
2. b) R. Filler, Fluorine Containing Drugs in Organofluorine Chemicals and their Industrial Application, Pergamon, New York, 1979, chapter 6;
3. c) M. Hudlicky, Chemistry of Organic Compounds, Ellis Horwood, Chichester, 1992.
4. See also: ; d) T. Ryckmanns, L. Balancon, O. Berton, C. Genicot, Y. Lamberty, B. Lallemand, P. Passau, N. Pirlot, L. Quéré, P. Talaga, Bioorg. Med. Chem. Lett. 2002, 12, 261-264;
5. e) M. S. Malamas, J. Sredy, C. Moxham, A. Katz, W. Xu, R. McDevitt, F. O. Adebayo, D. R. Sawicki, L. Seestaller, D. Sullivan, J. R. Taylor, J. Med. Chem. 2000, 43, 1293-1310;
6. f) A. J. Ciha, P. G. Ruminski, J. Agric. Food Chem. 1991, 39, 2072-2076.
7. a) H. Schmidbaur, O. Kumberger, Chem. Ber. 1993, 126, 3-9;
8. b) M. B. Dinger, W. Henderson, J. Organomet. Chem. 1998, 560, 233-243;
9. c) J. Liedtke, S. Loss, C. Widauer, H. Grützmacher, Tetrahedron 2000, 56, 143-156.
10. See for example: a) S. Schneider, C. C. Tzschucke, W. Bannwarth, Multiphase Homogeneous Catalysis (Eds.: B. Cornils, W. A. Herrmann, I. T. Horvath, W. Leitner, S. Mecking, H. Olivier-Booubigou, D. Vogt), Wiley VCH, 2005, Chapter 4, 346-354;
11. b) D. Clarke, M. A. Ali, A. A. Clifford, A. Parratt, P. Rose, D. Schwinn, W. Bannwarth, C. M. Rayner, Curr. Top. Med. Chem. 2004, 4, 729-771.
12. a) A. Wittkopp, P. R. Schreiner, The chemistry of dienes and polyenes, vol. 2, John Wiley & Sons, Chichester, 2000;
13. b) P. R. Schreiner, Chem. Soc. Rev. 2003, 32, 289-296;
14. c) A. Wittkopp, P. R. Schreiner, Chem. Eur. J. 2003, 9, 407-414;
15. d) C. M. Kleiner, P. R. Schreiner, Chem. Commun. 2006, 4315-4317;
16. e) M. Kotke, P. R. Schreiner, Synthesis 2007, 779-790.
17. Review: S. B. Tsogoeva, Eur. J. Org. Chem. 2007, 1701-1716.
18. Review: M. A. McClinton, D. A. McClinton, Tetrahedron 1992, 48, 6555-6666.
19. a) J. M. Paratian, S. Sibille, J. Périchon, J. Chem. Soc. Chem. Commun. 1992, 53-54;
20. b) M. Tordeux, B. Langlois, C. Wakselman, J. Chem. Soc. Perkin Trans. 1 1990, 2293-2299.
21. W. Ding, J. Pu, C. Zhang, Synthesis 1992, 635-637.
22. a) H.-P. Guan, C.-M. Hu, Synthesis 1996, 1363-1370;
23. b) H.-P. Guan, C.-M. Hu, J. Fluorine Chem. 1996, 78, 101-102;
24. c) H.-P. Guan, Q.-S. Hu, C.-M. Hu, Chin. J. Chem. 1996, 14, 87-91.
25. a) E. Marzi, F. Mongin, A. Spitaleri, M. Schlosser, Eur. J. Org. Chem. 2001, 2911-2915;
26. b) W. Dmowski, K. Piasecka-Maciejewska, J. Fluorine Chem. 1996, 78, 59-63.
27. a) A. B. Abubakar, B. L. Booth, N. N. E. Suliman, A. E. Tipping, J. Fluorine Chem. 1992, 56, 359-371;
28. b) M. G. Barlow, N. N. E. Suliman, A. E. Tipping, J. Fluorine Chem. 1995, 70, 59-69.
29. a) D. M. Volochnyuk, A. N. Kostyuk, D. A. Sibgatulin, A. N. Chernega, A. M. Pinchuk, A. A. Tolmachev, Tetrahedron 2004, 60, 2361-2371:
30. b) D. M. Volochnyuk, A. N. Kostyuk, D. A. Sibgatulin, A. N. Chernega, Tetrahedron 2005, 61, 2839-2847.
31. a) N. P. Gambaryan, L. A. Simonyan, P. V. Petrovskii, Izv. Akad. Nauk SSSR, Ser. Khim. 1967, 918-921;
32. b) M. Hojo, R. Masuda, Y. Kokuryo, H. Shioda, S. Matsuo, Chem. Lett. 1976, 499-502;
33. c) M. Hojo, R. Masuda, S. Sakaguchi, M. Takagawa, Synthesis 1986, 1016-1017;
34. d) A. Colla, M. A. P. Martins, G. Clar, S. Krimmer, P. Fischer, Synthesis 1991, 483-486;
35. e) M. Hojo, R. Masuda, E. Okada, Synthesis 1989, 215-217.
36. Reviews: a) V. G. Nenaidenko, A. V. Sanin, E. S. Balenkova, Russ. Chem. Rev. 1999, 68, 437-458;
37. b) T. Billard. Chem. Eur. J. 2006, 12, 974-979;
38. c) S. V. Druzhinin, E. S. Balenkova, V. G. Nenajdenko, Tetrahedron 2007, 63, 7753-7808.
39. N. Zanatta, R. Barichello, H. G. Bonacorso, M. A. P. Martins, Synthesis 1999, 765-768.
40. C. Mamat, T. Pundt, A. Schmidt, P. Langer, Tetrahedron Lett. 2006, 47, 2183-2185.
41. For a review of [3+3] cyclizations of 1,3-bis(silyl enol ethers) see: H. Feist, P. Langer, Synthesis 2007, 327-347.
42. a) T.-H. Chan, P. Brownbridge, J. Am. Chem. Soc 1980, 102, 3534-3538;
43. b) T. H. Chan, M. A. Brook, Tetrahedron Lett. 1985, 26, 2943-2946.
44. For a review of 1,3-bis(silyl enol ethers) in general, see: P. Langer, Synthesis 2002, 441-459.
45. T. Moriguchi, T. Endo, J. Org. Chem. 1995, 60, 3523-3528.
46. B. M. Trost, J. M. Balkovec, M. K. T. Mao, J. Am. Chem. Soc. 1983, 105, 6755-6757.
47. F. Effenberger, R. Maier, K.-H. Schönwälder, T. Ziegler, Chem. Ber. 1982, 115, 2766-2782.
48. 19F-NMR-Spektroskopie, Thieme, Stuttgart, 1994, p. 36.
49. CCDC-644284 (compound 4g), -644286 (compound 9c), -657293 (compound 17b), -644290 (compound 17d), and -644291 (compound 20a) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
50. H. G. Bonacorso, M. B. Costa, S. Moura, L. Pizzuti, M. A. P. Martins, N. Zanatta, A. F. C. Flores, J. Fluorine Chem. 2005, 126, 1396-1402.
51. A. F. C. Flores, G. M. Siqueira, R. Freitag, N. Zanatta, M. A. P. Martins, Quim. Nova 1994, 17, 298-300.
52. U. Schmidt, P. Grafen, Justus Liebigs Ann. Chem. 1962, 656, 97-102.
53. a) D. V. Sevenard, G.-V. Röschenthaler, Monatsh. Chem. 2001, 132, 911-918;
54. b) K. A. K. Ebraheem, Monatsh. Chem. 1991, 122, 157-163.
55. S. Nimgirawath, E. Ritchie, W. C. Taylor, Aust. J. Chem. 1976, 29, 339-356.
56. a) M. A. P. Martins, G. P. Bastos, H. G. Bonacorso, N. Zanatta, A. F. C. Flores, G. M. Siqueira, Tetrahedron Lett. 1999, 40, 4309-4312;
57. b) M. A. P. Martins, W. Cunico, G. M. Siqueira, V. L. Leidens, N. Zanatta, H. G. Bonacorso, A. F. C. Flores, J. Braz. Chem. Soc. 2005, 16, 275-279.
58. W. Cunico, C. A. Cechinel, H. G. Bonacorso, M. A. P. Martins, N. Zanatta, M. V. N. de Souza, I. O. Freitas, R. P. P. Soares, A. U. Krettli, Bioorg. Med. Chem. Lett. 2006, 16, 649-653.
59. a) J. M. Mellor, G. Reid, A. H. El-Sagheer, E. H. El-Tamany, Tetrahedron 2000, 56, 10039-10055;
60. b) Q. Chu, L. Song, G. Jin, S. Zhu, J. Fluorine Chem. 2001, 108, 51-56.
61. a) S. Zhu, G. Xu, C. Qin, Q. Chu, Y. Xu, Monatsh. Chem. 1999, 130, 671-680;
62. b) C. C. Madruga, E. Clerici, M. A. P. Martins, N. Zanatta, J. Heterocycl. Chem. 1995, 32, 735-738.
63. G. M. Sheldrick, SHELX97: Programs for Crystal Structure Analysis (Release 97-2), University of Göttingen, Germany, 1997.