Cleavage of tetrahydrofuran by tert-butyldimethylsilyl iodide and further transformations of the resulting 1-silyloxy-4-iodobutane

Synthesis (Germany)

Volumn 1988, Issue 1, 1988, Pages 56-58

  Nyström, Jan Erik ^a,b,c   McCanna, Terrence D ^a,b,c   Helquist, Paul ^a,b,c   Amouroux, Roger ^a,b,c  

^a ROYAL INSTITUTE OF TECHNOLOGY   (Sweden)

^b UNIVERSITY OF NOTRE DAME   (United States)

^c UNIVERSITÉ LYON 1   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84989004968     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-1988-27463     Document Type: Article

References (33)

1. Visiting Senior Research Fellow at Notre Dame, 1984-1985. Address correspondence to this author at the Royal Institute of Technology.
2. For some recent examples of the use of derivatives of type 1 in organic synthesis, see: Ley, S.V., Lygo, B., Sternfeld, F., Wonnacott, A. Tetrahedron 1986, 42, 4333.
3. Ley, S.V., Lygo, B., Wonnacott, A. Tetrahedron Lett. 1985, 26, 535.
4. Fox, C.M.J., Ley, S.V., Slawin, A.M.Z., Williams, D.J. J. Chem. Soc. Chem. Commun. 1985, 1805.
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6. Daalman, L., Newton, R.F., Pauson, P.L., Taylor, R.G., Wads-worth, A. J. Chem. Res. (S.) 1984, 344.
7. Carruthers, W., Gumming, S.A. J. Chem. Perkin Trans. 1 1983, 2383.
8. Michelot, D. Synthesis 1983, 139.
9. Takahashi, T., Ikeda, H., Tsuji, J. Tetrahedron Lett. 1981, 22, 1363.
10. Welch, S.C., Rao, A.C.S.P., Gibbs, C.G., Wong, R.Y. J. Org. Chem. 1980, 45, 4077.
11. Hungerbuehler, E., Naef, R., Wasmuth, D., Seebach, D., Loosli, H.R., Wehrli, A. Helv. Chim. Acta 1980, 63, 1960.
12. Heather, J.B., Sood, R., Price, P., Peruzzotti, G.P., Lee, S.S., Lee, L.-F.H., Sih, C.J. Tetrahedron Lett. 1973, 2313.
13. We note that uses of 3 are described in Ref. 2 (Ley et. at.), but the source of this compound is not reported.
14. Voronkov, M.G., Puzanova, V.E., Bubinskaya, E.I. Bull. Acad. Sci. USSR, Ser. Chem. 1975, 377.
15. Kohama, S., Imai, J, Kagaku To Kogyo (Osaka) 1984, 58, 46; C.A. 1984, 101, 7269.
16. Kricheldorf, H.R., Morber, G., Regel, W. Synthesis 1981, 383.
17. It has been reported that some metal oxides can promote the cleavage of tetrahydrofuran by trimethylsilyl chloride: Kawakami, Y., Yamashita, Y. Synth. Commun. 1982, 12, 253.
18. Corey, E.J., Venkateswarlu, A. J. Am. Chem. Soc. 1972, 94, 6190.
19. Greene, T.W. Protective Groups in Organic Synthesis, John Wiley & Sons, New York, 1981.
20. For brief reports of the use of (m-butyldimethylsilyl derivatives in some of our earlier work directed to other goals, see: Amouroux, R. Heterocycles 1984, 22, 1489.
21. Nystrom, J.-E, McCanna, T.D., Helquist, P., Iyer, R.S. TetraÂhedron Lett. 1985, 26, 5393.
22. For early studies of other silyloxy derivatives, see: Kruerke, U. Chem. Ber. 1962, 95, 174.
23. For some previous uses of ter/-butyldimethylsilyl iodide, see: Detty, M.R. J. Org. Chem. 1980, 45, 924.
24. Donike, M., Zimmermann, J. J. Chromatogr. 1980, 202. 483.
25. Detty, M.R., Seidler, M.D. J. Org. Chem. 1981, 46, 1283.
26. Detty, M.R., Seidler, M.D. Tetrahedron Lett. 1982, 25, 2543.
27. The in situ method for generation of trimethylsilyl iodide has been reported: Olah, G.A., Narany, S.C., Gupta, B.G.B., Malhotra, R. J. Org. Chem. 1979, 44, 1247.
28. Schmidt, A.M., Russ, M. Chem. Ztg. 1978, 102, 26 und 65.
29. If water is present during the cleavage of tetrahydrofuran, 3 will be contaminated with bis(terf-butyldimethylsilyl) ether (6): 'H-NMR (200 MHz): <5 = 0.03 (s, 12 H, CH3Si); 0.88 (s, 18 H, CH3C).
30. For reference purposes, l-(7£Ti-butyldimethylsilyloxy)butane 5 was prepared from butanol and ter;-butyldimethylsilyl chloride.4 The chemical shifts in the 13C spectrum of 4d show up-field deuterium-isotopic shift for all four carbons in the butyl chain relative to 5:-0.33 (C-4),-0.19 (C-3),-0.14 (C-2),-0.09 (C-l) ppm.
31. 13C-NMR data of phosphonates related to 4e has been reported recently: Zhao, Y.-F., Yan, S.-J., J. Org. Chem. 1985, 50, 2136.
32. Brown, C.A. J. Org. Chem. 1974, 39, 3913.
33. When 3 was allowed to react with the lithium enolate of cyclohexa-none under the same conditions (THF, 0°C, 5h). less than 5% conversion to 4 was observed (GLC).