An efficient synthesis of 5-silyl-2,3-dihydrofurans via acid-catalyzed ring-enlargement of cyclopropyl silyl ketones and their functionalization

Tetrahedron Letters

Volumn 46, Issue 43, 2005, Pages 7345-7348

  Honda, Mitsunori ^a   Naitou, Tomoyuki ^a   Hoshino, Hiromitsu ^a   Takagi, Seiji ^a   Segi, Masahito ^a   Nakajima, Tadashi ^a  

^a KANAZAWA UNIVERSITY   (Japan)

Author keywords

Cyclopropyl silyl ketone; Dihydrofurane; Heck reaction; Ring enlargement

Indexed keywords

ACID; ANION; ENOYL COENZYME A HYDRATASE; FURAN DERIVATIVE; KETONE DERIVATIVE; PROPANE; REAGENT; SILANE DERIVATIVE; TRIFLUOROMETHANESULFONIC ACID; TRIMETHYLSILYL DERIVATIVE;

ARTICLE; ATOM; CATALYST; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 25444469913     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.08.117     Document Type: Article

References (42)

1. For recent reviews on the synthesis and reaction of acylsilanes, see: M.A. Brook Silicon in Organic, Organometallic, and Polymer Chemistry 2000 John Wiley & Sons New York
2. B.F. Bonini, M. Comes-Franchini, M. Fochi, G. Mazzanti, and A. Ricci J. Organomet. Chem. 567 1998 181 189
3. H. Qi, and D.P. Curran Acyl Silicon, Germanium, or Boron Functions A.R. Katrizky O. Meth-Cohn C.W. Rees C.J. Moody Comprehensive Organic Functional Group Transformations: Synthesis: Carbon with Two Attached Heteroatoms with at Least One Carbon-to-Heteroatom Multiple Link Vol. 5, Chapter 5.09 1995 Pergamon Press Oxford 409 433
4. P.F. Cirillo, and J.S. Panek Org. Prep. Proced. Int. 24 1992 553 582
5. P.C.B. Page, S.S. Klair, and S. Rosenthal Chem. Soc. Rev. 19 1990 147 195
6. A. Ricci, and A. Degl'Innocenti Synthesis 1989 647 660
7. For reports about synthesis and reaction of cyclopropyl silyl ketones, see: R.L. Danheiser, and D.M. Fink Tetrahedron Lett. 26 1985 2513 2516
8. M.E. Scheller, and B. Frei Helv. Chim. Acta 69 1986 44 52
9. T. Nakajima, M. Tanabe, K. Ohno, M. Segi, and S. Suga Chem. Lett. 1986 177 180
10. J. Kang, J.H. Lee, K.S. Kim, J.U. Jeong, and C. Ryun Tetrahedron Lett. 28 1987 3261 3262
11. J.S. Nowick, and R.L. Danheiser Tetrahedron 44 1988 4113 4134
12. J. Clayden, D.W. Watson, and M. Chambers Tetrahedron 61 2005 3195 3203
13. T. Nakajima, M. Segi, F. Sugimoto, R. Hioki, S. Yokota, and K. Miyashita Tetrahedron 49 1993 8343 8358
14. T. Nakajima, M. Segi, T. Mituoka, Y. Fukute, M. Honda, and K. Naitou Tetrahedron Lett. 36 1995 1667 1670
15. M. Honda, Y. Yamamoto, H. Tuchida, M. Segi, and T. Nakajima Tetrahedron Lett. 46 2005 6465 6468
16. For reviews on the cyclopropane chemistry, see: Small Ring Compounds in Organic Synthesis I-V A. de Meijere Topics in Current Chemistry Vols. 133, 135, 144, 155, 178 1986, 1987, 1988, 1990, 1996 Springer Berlin, Heidelberg
17. H.N.C. Wong, M.-Y. Hon, C.-W. Tse, Y.-C. Yip, J. Tanko, and T. Hudlicky Chem. Rev. 89 1989 165 198
18. A. de Meijere, and L. Wessjohann Synlett 1990 20 32
19. D.W. Boykin Jr., and R.E. Lutz J. Am. Chem. Soc. 86 1964 5046 5047
20. E. Lee-Ruff, and P. Khazanie Can. J. Chem. 53 1975 1708 1713
21. M.P. Cook Jr. J. Org. Chem. 44 1979 2461 2468
22. V.K. Yadav, and R. Balamurugan Org. Lett. 3 2001 2717 2719
23. For reports about synthesis of 5-silyl-2,3-dihydrofuran, see: K. Miwa, T. Aoyama, and T. Shioiri Synlett 1994 461 462
24. P.J. Kocieñski, M. Pritchard, S.N. Wadman, R.J. Whitby, and C.L. Yeates J. Chem. Soc., Perkin Trans. 1 1992 3419 3429
25. For reports about reaction of vinylsilane with electrophilic reagent, see: T.A. Blumenkopf, and L.E. Overman Chem. Rev. 86 1986 857 873
26. R.B. Miller, and G. McGarvey J. Org. Chem. 43 1978 4424 4431
27. F. Cooke, R. Moerck, J. Schwindeman, and P. Magnus J. Org. Chem. 45 1980 1046 1053
28. For reports about reaction of vinylsilane with N-halosuccinimide, see: T. Wong, M.W. Tjepkema, H. Audrain, P.D. Wilson, and A.G. Fallis Tetrahedron Lett. 37 1996 755 758
29. D.P. Stamos, A.G. Taylor, and Y. Kishi Tetrahedron Lett. 37 1996 8647 8650
30. For reports about Heck type reaction of vinylsilane, see: C.D. Daves Jr., and A. Hallberg Chem. Rev. 89 1989 1433 1445
31. K. Kikukawa, K. Ikenaga, K. Kono, K. Toritani, F. Wada, and T. Matsuda J. Organomet. Chem. 270 1984 277 282
32. K. Ikenaga, K. Kikukawa, and T. Matsuda J. Chem. Soc., Perkin Trans. 1 1986 1959 1964
33. For reports about palladium-catalyzed cross-coupling reaction of vinylsilane in the presence of fluoride ion, see: Y. Hatanaka, and T. Hiyama Synlett 1991 845 853
34. K. Tamao, K. Kobayashi, and Y. Ito Tetrahedron Lett. 30 1989 6051 6054
35. Y. Hatanaka, and T. Hiyama Tetrahedron Lett. 31 1990 2719 2722
36. Y. Hatanaka, K. Goda, and T. Hiyama J. Organomet. Chem. 465 1994 97 100
37. For reports about Heck type reaction of 2,3-dihydrofuran, see: R.C. Larock, and W.H. Gong J. Org. Chem. 55 1990 407 408
38. S. Hillers, and O. Reiser Tetrahedron Lett. 34 1993 5265 5268
39. For reports about asymmetric Heck reaction of 2,3-dihydrofuran, see: F. Ozawa, A. Kubo, and T. Hayashi J. Am. Chem. Soc. 113 1991 1417 1419
40. F. Ozawa, Y. Kobatake, and T. Hayashi Tetrahedron Lett. 34 1993 2505 2508
41. For a review about the acidity and the synthetic use of TMSOTf as Lewis acid, see: A. Hosomi, and K. Miura H. Yamamoto L.M. Harwood C.J. Moody Lewis Acid Reagents: A Practical Approach 1999 Oxford University Press New York Chapter 8, pp 159-168
42. For a report about formation of γ-lactone from 5-silyl-2,3- dihydrofuran via Wacker type oxidation, see: P. Compain, J. Goré, and J.-M. Vatèle Tetrahedron 52 1996 10405 10416