Chromium mediated stereoselective synthesis of (Z)-1-fluoro-2-alkenyl alkyl and trialkylsilyl ethers from dibromofluoromethylcarbinyl ethers

Tetrahedron Letters

Volumn 46, Issue 32, 2005, Pages 5257-5261

  Nakagawa, Muga ^a   Saito, Akio ^a   Soga, Aiko ^a   Yamamoto, Natsuko ^a   Taguchi, Takeo ^a  

^a TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES   (Japan)

Author keywords

Chromium salt; Dibromofluoromethylcarbinol; Fluoroalkene; Fluoroenol ether

Indexed keywords

ALKENE DERIVATIVE; CHROMIUM CHLORIDE; ETHER DERIVATIVE; MANGANESE;

ARTICLE; CATALYST; CHEMICAL REACTION; COMBINATORIAL CHEMISTRY; DRUG SYNTHESIS; QUANTUM YIELD; STEREOCHEMISTRY; STEREOISOMERISM;

EID: 21844480112     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.06.035     Document Type: Article

References (61)

1. T. Hiyama H. Yamamoto Organofluorine Compounds: Chemistry and Applications 2000 Springer Berlin
2. R.D. Chambers Organofluorine Chemistry: Fluorinated Alkenes and Reactive Intermediates Top. Curr. Chem. Vol. 192 1997 Springer Berlin
3. T. Allemendinger, E. Felder, and E. Hungerbuhler J.T. Welch Selective Fluorination in Organic and Bioorganic Chemistry ACS Symposium Series 456 1991 ACS Washington, DC 186 195
4. J.T. Welch, J. Lin, L.G. Boros, B. DeCorte, K. Bergmann, and R. Gimi I. Ojima J.R. McCarthy J.T. Welch Biomedical Frontiers of Fluorine Chemistry ACS Symposium Series 639 1996 ACS Washington, DC 129 142
5. D.J. Burton, Z.-Y. Yang, and W. Qiu Chem. Rev. 96 1996 1641
6. J. Xu, and D.J. Burton Org. Lett. 4 2002 831
7. M. Okada, Y. Nakamura, A. Sato, H. Horikawa, A. Saito, and T. Taguchi Tetrahedron Lett. 43 2002 5845
8. Y. Nakamura, M. Okada, A. Sato, H. Horikawa, M. Koura, A. Saito, and T. Taguchi Tetrahedron 61 2005 5741
9. S. Sano, K. Saito, and Y. Nagao Tetrahedron Lett. 44 2003 3987
10. X. Lei, G. Dutheuil, X. Pannecoucke, and J.-C. Quirion Org. Lett. 6 2004 2101
11. Typical examples of difluoro enol ethers, M. Yamanaka, T. Ishihara, and T. Ando Tetrahedron Lett. 24 1983 507
12. Z.-M. Qiu, and D.J. Burton J. Org. Chem. 60 1995 5570
13. F.-Q. Jin, Y.-Y. Xu, and W.-Y. Huang J. Chem. Soc., Perkin Trans. 1 1993 795
14. Y. Kodama, H. Yamane, M. Okumura, M. Shiro, and T. Taguchi Tetrahedron 45 1995 12217
15. Y. Kodama, M. Okumura, N. Yanabu, and T. Taguchi Tetrahedron Lett. 37 1996 1061
16. H. Amii, T. Kobayashi, Y. Hanamoto, and K. Uneyama Chem. Commun. 1999 1323
17. H. Berber, T. Brigaud, O. Lefebvre, R. Plantier-Royon, and C. Portella Chem. Eur. J. 7 2001 903
18. T. Kobayashi, H. Tanaka, H. Amii, and K. Uneyama Tetrahedron 59 2003 1547
19. K. Uneyama, H. Tanaka, S. Kobayashi, M. Shioyama, and H. Amii Org. Lett. 6 2004 2733
20. Typical examples of difluoro ketene silyl acetal, O. Kitagawa, T. Taguchi, and Y. Kobayashi Tetrahedron Lett. 29 1988 1803
21. T. Taguchi, O. Kitagawa, Y. Suda, S. Okawa, A. Hashimoto, Y. Iitaka, and Y. Kobayashi Tetrahedron Lett. 29 1988 5291
22. K. Iseki, Y. Kuroki, D. Asada, and Y. Kobayashi Tetrahedron Lett. 38 1997 1447
23. Difluorodienes, T. Taguchi, Y. Kodama, and M. Kanazawa Carbohydr. Res. 249 1993 243
24. F.-Q. Jin, Y.-Y. Xu, and W.-Y. Huang J. Chem. Soc., Chem. Commun. 1993 814
25. H. Amii, T. Kobayashi, H. Terasawa, and K. Uneyama Org. Lett. 3 2001 3103
26. Monofluoro enol ethers, J.T. Welch, and K.W. Seper Tetrahedron Lett. 25 1984 5247
27. J.T. Welch, and J.S. Samartino J. Org. Chem. 50 1985 3663
28. H. Uno, K. Sakamoto, and H. Suzuki Bull. Chem. Soc. Jpn. 65 1992 218
29. T. Ishihara, K. Ichihara, and H. Yamanaka Tetrahedron 52 1996 255
30. G.K. Surya Prakash, J.B. Hu, and G.A. Olah J. Fluorine Chem. 112 2001 357
31. H. Hata, T. Kobayashi, H. Amii, K. Uneyama, and J.T. Welch Tetrahedron Lett. 43 2002 6099
32. X.-T. Hung, and Q.-Y. Chen J. Org. Chem. 67 2002 3231
33. S. Higashiya, W.L. Chung, D.S. Lim, S.C. Ngo, W.H. Kelly IV, P.J. Toscano, and J.T. Welch J. Org. Chem. 69 2004 6323
34. Monofluorodiene derivatives, G.-Q. Shi, and M. Schlosser Tetrahedron 49 1993 1445
35. D. Ntirampebura, and L. Ghosez Synthesis 2002 2043
36. For reviews of organochromium chemistry: A. Fürstner Chem. Rev. 99 1999 991
37. L.A. Wessjohann, and G. Scheid Synthesis 1999 1
38. T. Okazoe, K. Takai, and K. Uchimoto J. Am. Chem. Soc. 109 1987 951
39. R. Baati, D.K. Barma, J.R. Falck, and C. Mioskowski J. Am. Chem. Soc. 123 2001 9196
40. J.R. Falck, D.K. Barma, R. Baati, and C. Mioskowski Angew. Chem., Int. Ed. 40 2001 1281
41. R. Baati, D.K. Barma, U. Muraki Krishna, C. Mioskowski, and J.R. Falck Tetrahedron Lett. 43 2002 959
42. R. Bejot, S. Tisserand, M. Reddy, D.K. Barma, R. Baati, J.R. Falck, and C. Mioskowski Angew. Chem., Int. Ed. 44 2005 2008
43. C.-M. Hu, and J.J. Chen J. Chem. Soc., Chem. Commun. 1993 72
44. A.L. Marchese, and B.O. West J. Organomet. Chem. 266 1984 61
45. Recent reports on chromium mediated reaction using fluorinated substrates. D.K. Barma, A. Kundu, H.M. Zhang, C. Mioskowski, and J.R. Falck J. Am. Chem. Soc. 125 2003 3218
46. G. Dutheuil, X. Lei, X. Pannecoucke, and J.-C. Quirion J. Org. Chem. 70 2005 1911
47. Preliminary results of this paper were firstly reported at the 123rd Annual Meeting of Pharmaceutical Society of Japan, March 2003, Nagasaki, Japan; abstract-2, p 78.
48. 2 mediated fluoroalkenylation reaction of aldehyde using 1-bromo-1-fluoroalkenes. Saito, A; Nakagawa, M.; Taguchi, T. J. Fluorine Chem., in press.
49. H.C. Brown, and S. Narasimham J. Org. Chem. 47 1982 1604
50. M. Kuroboshi, N. Yamada, Y. Takebe, and T. Hiyama Synlett 1995 987
51. A. Fürstner, and N. Shi J. Am. Chem. Soc. 118 1996 2533
52. A. Fürstner, and N. Shi J. Am. Chem. Soc. 118 1996 12349
53. 2 slowly. K. Takai, K. Kimura, T. Kuroda, T. Hiyama, and H. Nozaki Tetrahedron Lett. 24 1983 5281
54. R. Grigg, B. Putnikovic, and C.J. Urch Tetrahedron Lett. 38 1997 6307
55. T. Lübbers, and H.J. Schäfer Synlett 1992 743
56. C. Hackmann, and H.J. Schäfer Tetrahedron 49 1993 4559
57. D.K. Barma, A. Kundu, R. Baati, C. Mioskowski, and J.R. Falck Org. Lett. 4 2002 1387
58. K. Takai, R. Kokumai, and T. Nobunaka Chem. Commun. 2001 1128
59. Z selective formation of chlorovinyl silyl ether via lithium carbenoid derived from trichloromethylcarbinyl silyl ether with BuLi was reported. M.C. Pirrung, and J.R. Hwu Tetrahedron Lett. 24 1983 565
60. Tomioka and Moss reported the stereochemistry of hydrogen-1,2-shift of β-alkoxyhalocarbenes leading to 2-halovinyl ethers including fluoro derivative. H. Tomioka, T. Sugiura, Y. Masumoto, Y. Izawa, S. Inagaki, and K. Iwase J. Chem. Soc., Chem. Commun. 1986 693
61. R.A. Moss, G.-J. Ho, and W. Liu J. Am. Chem. Soc. 114 1992 959