Cyclobutane ring formation by triflic imide catalyzed [2+2]-cycloaddition of allylsilanes

Tetrahedron Letters

Volumn 47, Issue 34, 2006, Pages 6053-6056

  Takasu, Kiyosei ^a   Hosokawa, Norihiko ^a   Inanaga, Kazato ^a   Ihara, Masataka ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

2+2 Cycloaddition; Acrylonitrile; Allylsilane; Catalyst; Cyclobutane; Equilibrium; Triflic imide

Indexed keywords

CYCLOBUTANE; IMIDE; SILANE DERIVATIVE;

ARTICLE; CATALYST; CHEMICAL REACTION; CYCLOADDITION; ELECTRON; ENVIRONMENTAL TEMPERATURE; THERMODYNAMICS;

EID: 33746001410     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.06.102     Document Type: Article

References (29)

1. Lee-Ruff E., and Mladenova G. Chem. Rev. 103 (2003) 1449-1483 and references cited therein
2. Namyslo J.C., and Kaufmann D.E. Chem. Rev. 103 (2003) 1485-1537 and references cited therein
3. Baldwin J.E. In: Trost B.M., and Fleming I. (Eds). Comprehensive Organic Synthesis Vol. 5 (1991), Pergamon Press, Oxford 63-84
4. Crimmins M.T. In: Trost B.M., and Fleming I. (Eds). Comprehensive Organic Synthesis Vol. 5 (1991), Pergamon Press, Oxford 123-150
5. Takasu K., Ueno M., Inanaga K., and Ihara M. J. Org. Chem. 69 (2004) 517-521
6. 2NH-catalyzed reactions;. Boxer M.B., and Yamamoto H. J. Am. Chem. Soc. 128 (2006) 48-49
7. Zhang L., and Kozmin S.A. J. Am. Chem. Soc. 126 (2004) 10204-10205
8. Ishihara K., Hiraiwa Y., and Yamamoto H. Synlett (2001) 1851-1854
9. Cossy J., Lutz F., Alauze V., and Meyer C. Synlett (2002) 45-48
10. Inanaga K., Takasu K., and Ihara M. J. Am. Chem. Soc. 127 (2005) 3668-3669
11. Knölker H.-J., Baum G., and Graf R. Angew. Chem., Int. Ed. Engl. 33 (1994) 1612-1615
12. Knölker H.-J., Baum E., and Schmitt O. Tetrahedron Lett. 39 (1998) 7705-7708
13. Examples for [2+2]-cycloaddition of allylsilanes in the presence of a stoichiometric amount of Lewis acid: with α,β-unsaturated esters:. Organ M.G., Dragan V., Miller M., Froese R.D.J., and Goddard J.D. J. Org. Chem. 65 (2000) 3666-3678
14. with propiolate:. Monti H., Audran G., Léandri G., and Monti J.-P. Tetrahedron Lett. 35 (1994) 3073-3076
15. with α,β-unsaturated lactams:. Brengel G.P., Rithner C., and Meyers A.I. J. Org. Chem. 59 (1994) 5144-5146
16. with α,β-unsaturated diesters:. Yamanaka T., and Akiyama M. Tetrahedron Lett. 39 (1998) 7885-7888
17. As a correlated study, electrocatalytic [2+2]-cycloaddition of allylsilanes with enol ethers has been reported. Chiba K., Miura T., Kim S., Kitano Y., and Tada M. J. Am. Chem. Soc. 123 (2001) 11314-11315
18. Reviews for cycloaddition reactions of allylsilanes;. Hosomi A. Acc. Chem. Res. 21 (1988) 200-206
19. Knölker H.-J. J. Prakt. Chem. 339 (1997) 304-314
20. Masse C.E., and Panek J.S. Chem. Rev. 95 (1995) 1293-1316
21. 2Si: C, 67.54 ; H, 11.34; found: C, 67.28; H, 11.01.
22. Compound 4a was obtained as a mixture of inseparable diastereomers, and stereochemistry of each diastereomers was not determined.
23. 6a).
24. Mathieu B., and Ghosez L. Tetrahedron Lett. 38 (1997) 5497-5500
25. Vij A., Zheng Y., Kirchmeier R.L., and Shreeve J.M. Inorg. Chem. 33 (1994) 3281-3288
26. Mathieu B., and Ghosez L. Tetrahedron 58 (2002) 8219-8226
27. Danheiser R.L., Dixon B.R., and Gleason R.W. J. Org. Chem. 57 (1992) 6094-6097
28. Knölker H.-J., Jones P.G., and Panek J.-B. Synlett (1990) 429-430
29. Knölker H.-J., Jones P.G., and Wanzl G. Synlett (1998) 613-616 and references cited therein