The nucleophilic 5-endo-trig cyclization of 1,1-difluoro-1-alkenes: Ring-fluorinated hetero- and carbocycle synthesis and remarkable effect of the vinylic fluorines on the disfavored process

Synthesis

Volumn , Issue 13, 2002, Pages 1917-1936

  Ichikawa, Junji ^a   Wada, Yukinori ^a   Fujiwara, Masaki ^a   Sakoda, Kotaro ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

Alkenes; Carbocycles; Cyclizations; Fluorine; Heterocycles

Indexed keywords

OLEFINS; SUBSTITUTION REACTIONS;

NUCLEOPHILES;

SYNTHESIS (CHEMICAL);

ALKENE; BENZOFURAN DERIVATIVE; BENZOTHIOPHENE DERIVATIVE; CARBON; FLUORINE DERIVATIVE; HYDROXYL GROUP; NITROGEN; OXYGEN; STYRENE DERIVATIVE; SULFUR; TOLUENESULFONAMIDE DERIVATIVE; VINYL DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; ESTERIFICATION; FLUORINATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; REPRODUCIBILITY; SYNTHESIS;

EID: 0036395596     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2002-33912     Document Type: Article

References (73)

1. Baldwin, J. E. J. Chem. Soc., Chem. Commun. 1976, 734.
2. Baldwin J. E.; Cutting, J.; Dupont, W.; Kruse, L.; Silberman, L.; Thomas, R. C. J. Chem. Soc., Chem. Commun. 1976, 736.
3. Baldwin, J. E.; Thomas, R. C.; Kruse, L. I.; Silberman, L. J. Org. Chem. 1977, 42, 3846.
4. For recent reports see: Jones, A. D.; Knight, D. W.; Hibbs, D. E. J. Chem. Soc., Perkin Trans. 1 2001, 1182; and references cited therein.
5. Bravo, F.; Kassou, M.; Castillón, S. Tetrahedron Lett. 1999, 40, 1187.
6. Andrey, O.; Ducry, L.; Landais, Y.; Planchenault, D.; Weber, V. Tetrahedron Lett. 1997, 40, 3267; and references cited therein.
7. Kimura, M.; Harayama, H.; Tanaka, S.; Tamaru, Y. J. Chem. Soc., Chem. Commun. 1994, 2531; and references cited therein.
8. For recent reports see: Parsons, A. F. C. R. Acad. Sci. 2001, 4, 391; and references cited therein.
9. Bommezijn, S.; Martin, C. G.; Kennedy, A. R.; Lizos, D.; Murphy, J. A. Org. Lett. 2001, 3, 3405; and references cited therein.
10. Ishibashi, H.; Sato, T.; Ikeda, M. Synthesis 2002, 695.
11. Caldwell, J. J.; Craig, D.; East, S. P. Synlett 2001, 1602; and references cited therein.
12. Dell'Erba, C.; Mugnoli, A.; Novi, M.; Pani, M.; Petrillo, G.; Tavani, C. Eur. J. Org. Chem. 2000, 903; and references cited therein.
13. Auvray, P.; Knochel, P.; Normant, J. F. Tetrahedron Lett. 1985, 26, 4455.
14. Beak, P.; Wilson, K. D. J. Org. Chem. 1986, 51, 4627; and references cited therein.
15. Padwa, A.; Yeske, P. E. J. Am. Chem. Soc. 1988, 110, 1617.
16. Grigg, R.; Kemp, J.; Malone, J. F.; Rajviroongit, S.; Tangthongkum, A. Tetrahedron 1988, 44, 5361.
17. Tsuge, O.; Kanemasa, S.; Yamada, T.; Matsuda, K. J. Org. Chem. 1987, 52, 2523.
18. Thorimbert, S.; Malacria, M. Tetrahedron Lett. 1998, 39, 9659.
19. Gao, J.; Rusting, J. F. J. Org. Chem. 1998, 63, 218.
20. Ichikawa, J.; Wada, Y.; Okauchi, T.; Minami, T. Chem. Commun. 1997, 1537.
21. Ichikawa, J.; Fujiwara, M.; Wada, Y.; Okauchi, T.; Minami, T. Chem. Commun. 2000, 1887.
22. Ichikawa, J.; Wada, Y.; Sakoda, K. Chem. Lett. 2002, 282.
23. 5a examples based on the same concept have been reported: Yamazaki, T.; Hiraoka, S.; Sakamoto, J.; Kitazume, T. J. Phys. Chem. A 1999, 103, 6820.
24. Wang, Z.-G.; Hammond, G. B. J. Org. Chem. 2000, 65, 6547.
25. Coe, P. L.; Burdon, J.; Haslock, I. B. J. Fluorine Chem. 2000, 102, 43.
26. Volle, J.-N.; Schlosser, M. Eur. J. Org. Chem. 2000, 823.
27. Smart, B. E. In Organofluorine Chemistry Principles and Commercial Applications; Banks, R. E.; Smart, B. E.; Tatlow, J. C., Eds.; Plenum: New York, 1994, 57.
28. Lee, V. J. In Comprehensive Organic Synthesis, Vol. 4; Trost, B. M., Ed.; Pergamon: Oxford, 1991, 69.
29. Ichikawa, J.; Kobayashi, M.; Noda, Y.; Yokota, N.; Amano, K.; Minami, T. J. Org. Chem. 1996, 61, 2763.
30. For related ring constructions of in situ generated 1,1-difluoro-1-alkenes see: Strekowski, L.; Kiselyov, A. S.; Hojjat, M. J. Org. Chem. 1994, 59, 5886; and references cited therein.
31. Kiselyov, A. S.; Strekowski, L. Tetrahedron Lett. 1994, 35, 7597.
32. Silvester, M. J. Adv. Heterocycl. Chem. 1994, 59, 1.
33. Silvester, M. J. Aldrichimica Acta 1991, 24, 31.
34. Organofluorine Chemistry Principles and Commercial Applications; Banks, R. E.; Smart, B. E.; Tatlow, J. C., Eds.; Plenum: New York, 1994.
35. For the 6-endo-trig cyclization of 1,1-difluoro-1-alkenes see: Wada, Y.; Ichikawa, J.; Katsume, T.; Nohiro, T.; Okauchi, T.; Minami, T. Bull. Chem. Soc. Jpn. 2001, 74, 971.
36. Burdon, J.; Coe, P. L.; Haslock, I. B.; Powell, R. L. J. Fluorine Chem. 1997, 85, 151.
37. Ichikawa, J. J. Fluorine Chem. 2000, 105, 257; and references cited therein.
38. Ichikawa, J.; Minami, T.; Sonoda, T.; Kobayashi, H. Tetrahedron Lett. 1992, 33, 3779.
39. Ichikawa, J.; Fujiwara, M.; Nawata, H.; Okauchi, T.; Minami, T. Tetrahedron Lett. 1996, 37, 8799.
40. Ichikawa, J.; Ikeura, C.; Minami, T. Synlett 1992, 739.
41. Mitsunobu, O. Synthesis 1981, 1.
42. Henry, J. R.; Marcin, L. R.; McIntosh, M. C.; Scola, P. M.; Harris, G. D.; Weinreb, S. M. Tetrahedron Lett. 1989, 30, 5709.
43. Roush, W. R.; Dtraub, J. A.; Brown, R. J. J. Org. Chem. 1987, 52, 5127.
44. Hayashi, S.; Nakai, T.; Ishikawa, N.; Burton, D. J.; Naae, D. G.; Kesling, H. S. Chem. Lett. 1979, 983.
45. Kitazume, T.; Ohnogi, T. Synthesis 1988, 615.
46. Fuchikami, T.; Shibata, Y.; Suzuki, Y. Tetrahedron Lett. 1986, 27, 3173.
47. Hutchinson, D. K.; Fuchs, P. L. J. Am. Chem. Soc. 1987, 109, 4930.
48. For examples where N-substituents played an important role see: Tarnchompoo, B.; Thebtaranonth, C.; Thebtaranonth, Y. Tetrahedron Lett. 1987, 28, 6675.
49. Padwa, A.; Norman, B. H. J. Org. Chem. 1990, 55, 4801.
50. For the synthesis of 2- and 3-fluoroindoles see: Torres, J. C.; Garden, S. J.; Pinto, A. C.; da Silva, F. S. Q.; Boechat, N. Tetrahedron 1999, 55, 1881; and references cited therein..
51. For the synthesis of 2- and 3-fluorobenzo[b]furans see: Martín-Santamaría, S.; Carroll, M. A.; Carroll, C. M.; Carter, C. D.; Pike, V. W.; Rzepa, H. S.; Widdowson, D. A. Chem. Commun. 2000, 649.
52. Barton, D. H. R.; Hesse, R. H.; Jackman, G. P.; Pechet, M. M. J. Chem. Soc., Perkin Trans. 1 1977, 2604.
53. Bailey, J.; Plevey, R. G.; Tatlow, J. C. Tetrahedron Lett. 1975, 869.
54. For the synthesis of 2- and 3-fluorobenzo[b]thiophenes see: Shirley, I. M. J. Fluorine Chem. 1994, 66, 51.
55. Nussbaumer, P.; Petranyi, G.; Stütz, A. J. Med. Chem. 1991, 34, 65.
56. Bensoam, J.; Mathey, F. Tetrahedron Lett. 1977, 2797.
57. For the electrocyclization of 1,1-difluoro-1-alkenes see: Chambers, R. D.; Greenhall, M. P. J. Chem. Soc., Chem. Commun. 1990, 1128.
58. Burger, K.; Helmreich, B. J. Chem. Soc., Chem. Commun. 1992, 348.
59. For the synthesis of fluorofurans see: Forrest, A. K.; O'Hanlon, P. J. Tetrahedron Lett. 1995, 36, 2117; and references cited therein.
60. For the synthesis of fluoropyrroles see: Tajima, T.; Ishii, H.; Fuchigami, T. Tetrahedron Lett. 2001, 42, 4857.
61. Novikov, M. S.; Khlebnikov, A. F.; Sidorina, E. S.; Kostikov, R. R. J. Fluorine Chem. 1998, 90, 117; and references cited therein.
62. Qiu, Z.-M.; Burton, D. J. Tetrahedron Lett. 1995, 36, 5119; and references cited therein.
63. Leroy, J.; Wakselman, C. Tetrahedron Lett. 1994, 35, 8605; and references cited therein.
64. Barnes, K.; Hu, Y.; Hunt, D. Synth. Commun. 1994, 24, 1749.
65. For the synthesis of fluorothiophenes see: Chambers, R. J.; Marfat, A. Synth. Commun. 2000, 30, 3629.
66. Kobarfard, F.; Kauffman, J. M. J. Heterocycl. Chem. 1999, 36, 1247.
67. Andrés, D. F.; Laurent, E. G.; Marquet, B. S. Tetrahedron Lett. 1997, 38, 1049; and references cited therein.
68. Burger, K.; Helmreich, B. Heterocycles 1994, 39, 819; and references cited therein.
69. For the intramolecular carbolithiation of fluorine-free alkenes see: Yus, M.; Oritz, R.; Huerta, F. F. Tetrahedron Lett. 2002, 43, 2957; and references cited therein.
70. Strobach, D. R.; Boswell, G. A. Jr. J. Org. Chem. 1971, 36, 818.
71. Bailey, W. F.; Punzalan, E. R. J. Org. Chem. 1990, 55, 5404.
72. Negishi, E.; Swanson, D. R.; Rousset, C. J. J. Org. Chem. 1990, 55, 5406.
73. Topolsky, M. J. Org. Chem. 1995, 60, 5588.