Regio- and stereoselective reactions of gem-difluorinated vinyloxiranes with heteronucleophiles

Journal of Organic Chemistry

Volumn 70, Issue 23, 2005, Pages 9354-9363

  Ueki, Hisanori ^a   Kitazume, Tomoya ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACIDITY; CARBON; HALOGEN COMPOUNDS; STEREOCHEMISTRY;

DIASTEREOMERS; GEM-FLUORINATED VINYLOXIRANE; REGIOSELECTIVITY; STEREOSELECTIVITY;

ORGANIC COMPOUNDS;

1,2 EPOXY 3 BUTENE; ALLYL ALCOHOL; ALLYL COMPOUND; CARBON; EPOXIDE; HALOHYDRINE; LITHIUM DERIVATIVE; MAGNESIUM DERIVATIVE; UNCLASSIFIED DRUG;

ACIDITY; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; FLUORINATION; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; TEMPERATURE DEPENDENCE;

ARABINOSE; ETHYLENE OXIDE; HYDROCARBONS, FLUORINATED; LITHIUM COMPOUNDS; MODELS, CHEMICAL; OXIDATION-REDUCTION; STEREOISOMERISM;

EID: 27744551135     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo051468t     Document Type: Article

References (85)

1. (a) Smith, J. G. Synthesis 1984, 629.
2. (b) Rao, A. S.; Paknikar, S. K.; Kirtane, J. G. Tetrahedron 1983, 39, 2323.
3. (a) Bonini, C.; Righi, G. Tetrahedron 2002, 58, 4981.
4. (b) Porter, M. J.; Skidmore, J. Chem. Commun. 2000, 1215.
5. Some recent reports: (a) Nanayakkara, P.; Alper, H. J. Org. Chem. 2004, 69, 4686.
6. (b) Smith, A. B., III; Pitram, S. M.; Boldi, A. M.; Gaunt, M. J.; Sfouggatakis, C.; Moser, W. H. J. Am. Chem. Soc. 2003, 125, 14435.
7. (c) Bertozzi, F.; Crotti, P.; Del Moro, F.; Di Bussolo, V.; Macchia, F.; Pineschi, M. Eur. J. Org. Chem. 2003, 1264.
8. (d) Clark, J. S.; Myatt, J.; Wilson, C.; Roberts, L.; Walshe, N. Chem. Commun. 2003, 1546.
9. (e) Koizumi, T.; Akita, T.; Endo, T. Polym. J. 2003, 35, 266.
10. (f) Trost, B. M.; Brown, B. S.; McEachern, E. J.; Kuhn, O. Chem.-Eur. J. 2003, 9, 4442.
11. (g) Myers, A. G.; Siu, M. Tetrahedron 2002, 58, 6397.
12. (h) Takayama, H.; Arai, M.; Kitajima, M.; Aimi, N. Chem. Pharm. Bull. 2002, 50, 1141.
13. Bussolo, V. D.; Caselli, M.; Pineschi, M.; Crotti, P. Org. Lett. 2002, 4, 3695.
14. (j) Ji, M.; Choi, H.; Park, M.; Kee, M.; Jeong, Y. C.; Koo, S. Angew. Chem., Int. Ed. 2001, 40, 3627.
15. (k) Olofsson, B.; Khamrai, U.; Somfai, P. Org. Lett. 2000, 2, 4087.
16. (a) Yamazaki, T.; Ueki, H.; Kitazume, T. Chem. Commun. 2002, 2670.
17. (b) Ueki, H.; Chiba, T.; Yamazaki, T.; Kitazume, T. J. Org. Chem. 2004, 69, 7616.
18. (a) Ramachandran, P. V., Ed. Asymmetric Fluoroorganic Chemistry; ACS Symposium Series 746; American Chemical Society: Washington, DC, 2000.
19. (b) Soloshonok, V. A., Ed. EnantiocontrolledSynthesis of Fluoro-Organic Compounds; John Wiley & Sons: New York, 1999.
20. (c) Kitazume, T.; Yamazaki, T. Experimental Methods In Organic Fluorine Chemistry; Kodansya, Gordon and Breach: Tokyo, 1998.
21. (a) Submitted for publication,
22. (b) Ueki, H.; Kitazume, T. Tetrahedron Lett. 2005, 46, 5439.
23. (c) Ueki, H.; Chiba, T.; Kitazume, T. Org. Lett. 2005, 7, 1367.
24. (a) Taber, D. F.; Mitten, J. V. J. Org. Chem. 2002, 67, 3847.
25. (b) Söderberg, B. C.; Austin, L. R.; Davis, C. A.; Nyström, J.-E.; Vagberg, J. O. Tetrahedron 1994, 50, 61.
26. (c) Naruta, Y.; Maruyama, K. Chem. Lett. 1987, 963.
27. (d) Ent, H.; De Koning, H.; Speckamp, W. N. J. Org. Chem. 1986, 51, 1687.
28. (e) Rose, C. B.; Taylor, S. K. J. Org. Chem. 1974, 39, 578.
29. (f) Gasc, J. C.; Nédélec, L. Tetrahedron Lett. 1971, 2005.
30. (g) Anderson, R. J. J. Am. Chem. Soc. 1970, 92, 4978.
31. (h) Herr, R. W.; Johnson, C. R. J. Am. Chem. Soc. 1970,92,4979.
32. Rose, C. B.; Smith, C. W., Jr. Chem. Commun. 1969, 248.
33. (a) Canepa, C.; Tonachini, G. J. Org. Chem. 1996, 61, 7066.
34. (b) Yang, Z.-Y.; Burton, D. J. J. Org. Chem. 1991, 56, 1037.
35. (c) Tonachini, G.; Canepa, C. Tetrahedron 1989, 45, 5163.
36. (a) Hu, Q.-S.; Hu, C.-M. J. Fluorine Chem. 1997, 83, 87.
37. (b) Tsukamoto, T.; Kitazume, T. Synlett 1992, 977.
38. (c) Ishihara, T.; Miwatashi, S.; Kuroboshi, M.; Utimoto, K. Tetarahedron Lett. 1991, 32, 1069.
39. Yang, Z.-Y.; Burton, D. J. J. Fluorine Chem. 1989, 44, 339.
40. (a) Zhang, X.; Xia, H.; Dong, X.; Jin, J.; Meng, W.-D.; Qing, F.-L. J. Org. Chem. 2003, 68, 9026.
41. (b) Kirihara, M.; Takuwa, T.; Takizawa, S.; Momose, T.; Nemoto, H. Tetrahedron 2000, 56, 8275.
42. (c) Kirihara, M.; Takuwa, T.; Takizawa, S.; Momose, T. Tetrahedron Lett. 1997, 38, 2853.
43. (a) Guo, Y.; Chen, Q.-Y. J. Fluorine Chem. 2001, 707, 89.
44. (b) Kirihara, M.; Takuwa, T.; Okumura, M.; Wakikawa, T.; Takahata, H.; Momose, T.; Takeuchi, Y.; Nemoto, H. Chem. Pharm. Bull. 2000, 48, 885.
45. (c) Rajaonah, M.; Rock, M. H.; Bégué, J.-P.; Bonnet-Delpon, D.; Condon, S.; Nédélec, J.-Y. Tetrahedron Lett. 1998,39, 3137.
46. (d) Tellier, F.; Duffault, J.-M.; Baudry, M.; Sauvétre, R. J. Fluorine Chem. 1998, 91, 133.
47. (e) Shibuya, A.; Kurishita, M.; Ago, C.; Taguchi, T. Tetrahedron 1996, 52, 271.
48. (f) Oui, W.; Burton, D. J. J. Fluorine Chem. 1993, 65, 143.
49. (a) Nguyen, B. N.; Yang, Z.-Y.; Burton, D. J. J. Org. Chem. 1998, 63, 2887.
50. (b) Okano, T.; Shimizu, T.; Sumida, K.; Eguchi, S. J. Org. Chem. 1993, 58, 5163.
51. (c) Yu, Z.; Nguyen, B. V.; Burton, D. J. Synlett 1992, 141.
52. (a) Peng, W.; Zhu, S. Tetrahedron 2003, 59, 4395.
53. (b) Peng, W.; Zhu, S. Synlett 2003, 187.
54. (c) Golubev, A. S.; Pasternak, P. V.; Shidlovskii, A. F.; Saveléva, L. N.; Averkiev, B. B.; Nesterov, V. N.; Antipin, M. Y.; Peregudov, A. S.; Chkanikov, N. D. J. Fluorine Chem. 2002, 114, 63.
55. (d) Weimin, P.; Shizheng, Z.; Guifang, J. Tetrahedron 2001, 57, 5781.
56. (e) Bé;gué, J.-P.; Bonnet-Delpon, D.; Rock, M. H. Tetrahedron Lett. 1994, 35, 6097.
57. (a) Tellier, F.; Sauvétre, R. J. Fluorine Chem. 1996, 76, 79.
58. (b) Tellier, F.; Sauv́tre, R. Tetrahedron Lett. 1995, 36, 4221.
59. (a) Hurdrlik, P. F.; Misra, R. N.; Withers, G. P.; Hudrlik, A. M.; Rona, R. J.; Arcoleo, J. P. Tetrahedron Lett. 1976, 1453.
60. (b) Naqvi, S. M.; Horwitz, J. P.; Filler, R. J. Am. Chem. Soc. 1957, 79, 6283.
61. (c) House, H. O. J. Am. Chem. Soc. 1955, 77, 3070.
62. Persson, I. Pure Appl. Chem. 1986, 58, 1153.
63. (a) Díaz, D.; Martín, T.; Martín, V. J. Org. Chem. 2001, 66, 7231.
64. (b) Blaser, A.; Reymond, J.-L. Helv. Chim. Acta 2001, 84, 2119.
65. (c) Babudri, F.; Fiandanese, V.; Marchese, G.; Punzi, A. Tetrahedron 2001, 57, 549.
66. (d) Blaser, A.; Reymond, J.-L. Synlett 2000, 817-819.
67. (e) Daviu, N.; Delgado, A.; Llebaria, A. Synlett 1999, 1243.
68. (f) Guo, Z.-H.; Haines, A. H.; Taylor, J. K. Synlett 1993, 607.
69. (g) Andrews, G. C.; Crawford, T. C.; Contillo, L. G., Jr. Tetrahedron Lett. 1981, 22, 3803.
70. (a) Myers, A. G.; Siu, M.; Ren, F. J. Am. Chem. Soc. 2002,124, 4230.
71. (b) Myers, A. G.; Siu, M. Tetrahedron 2002, 58, 6397.
72. (c) Hecht, S.; Amslinger, S.; Jauch, J.; Kis, K.; Trentinaglia, V.; Adam, P.; Eisenreich, W.; Bacher, A.; Rohdich, F. Tetrahedron Lett. 2002, 43, 8929.
73. (d) Eletti-Bianchi, G.; Centini, F.; Re, L. J. Org. Chem. 1976, 41, 1648.
74. (a) Bajwa, J. S.; Anderson, R. C. Tetrahedron Lett. 1991, 32, 3021.
75. (b) Bartas-Yacoubou, J.-M.; Maduike, N.; Kyere, S.; Doan, L.; Whalen, D. L. Tetrahedron Lett. 2002, 43, 3781.
76. Durham, D.; Kingsbury, C. A. J. Chem. Soc., Perkin Trans. 2 1986, 923.
77. Oxirane-opening halogenations with retention of stereochemistry by gaseous HCl are reported. See: (a) Gilmore, A.; Lauret, C.; Roberts, S. M. Tetrahedron 2003, 59, 4363.
78. (b) Adger, B. M.; Barkley, J. V.; Bergeron, S.; Cappi, M. W.; Flowerdew, B. E.; Jackson, M. P.; McCague, R.; Nugent, T. C.; Roberts, S. M. J. Chem. Soc., Perkin Trans. 1 1997, 3501.
79. (c) Berti, G.; Macchia, B.; Macchia, F.; Monti, L. J. Chem. Soc. C 1971, 3371.
80. Ciaccio, J. A.; Addess, K. J.; Bell, T. W. Tetrahedron Lett. 1986, 27, 3697.
81. Yamazaki, T.; Hiraoka, S.; Sakamoto, J.; Kitazume, T. Org. Lett. 2001, 3, 743.
82. (a) Fukuzumi, S.; Ohkubo, K.; Okamoto, T. J. Am. Chem. Soc. 2002, 124, 14147.
83. (b) Fukuzumi, S.; Ohkubo, K. J. Am. Chem. Soc. 2002,124, 10270.
84. (c) Ohkubo, K.; Suenobu, T.; Imahori, H.; Orita, A.; Otera, J.; Fukuzumi, S. Chem. Lett. 2001, 978.
85. (d) Fukuzumi, S.; Ohkubo, K. Chem-Eur. J. 2000, 6, 4532.