Intramolecular [3+2] cycloaddition reaction of α,β-enoate derivatives having allylsilane parts: 1,1′-biphenyl-2,2′-di(triflyl)amide (BIPAM)+2Me2AlCl as a novel Lewis acid

Tetrahedron Letters

Volumn 47, Issue 25, 2006, Pages 4181-4185

  Saito, Akio ^a   Sakamoto, Wataru ^a   Yanai, Hikaru ^a   Taguchi, Takeo ^a  

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

Author keywords

[No Author keywords available]

Indexed keywords

1,1' BIPHENYL 2,2' DI(TRIFLYL)AMIDE; ALUMINUM CHLORIDE; AMIDE; ESTER DERIVATIVE; LEWIS ACID; SILANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL PROCEDURES; CHEMICAL REACTION; CYCLOADDITION; REACTION ANALYSIS;

EID: 33646510069     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.04.066     Document Type: Article

References (40)

1. Reviews:. Fleming I. In: Trost B.M., Fleming I., and Paquette L.A. (Eds). Comprehensive Organic Synthesis Vol. 2 (1991), Pergamon Press, Oxford, UK 563
2. Langkopf E., and Schinzer D. Chem. Rev. 95 (1995) 1375
3. Fleming I., Barbero A., and Walter D. Chem. Rev. 97 (1997) 2063
4. Laurent C., Philippe J., and Yannick L. Eur. J. Chem. (2004) 3173
5. Danheiser R.L., Takahashi T., Bertok B., and Dixon B.R. Tetrahedron Lett. 34 (1993) 3845
6. Knölker H.J., Foitzik N., Goesmann H., and Graf R. Angew. Chem., Int. Ed. Engl. 32 (1993) 1081
7. Knölker H.J., Jones P.G., and Graf R. Synlett (1996) 1155
8. Groaning M.D., Brengel G.P., and Meyers A.I. J. Org. Chem. 63 (1998) 5517
9. Akiyama T., Hoshi E., and Fujiyoshi S. J. Chem. Soc., Perkin Trans. 1 (1998) 2121
10. Peng Z.H., and Woerpel K.A. Org. Lett. 2 (2000) 1379
11. Knölker H.J., Baum G., and Graf R. Angew. Chem., Int. Ed. Engl. 33 (1994) 1612
12. Knölker H.J. J. Prakt. Chem. 339 (1997) 304
13. Knölker H.J., Baum G., Schmitt O., and Wanzl G. Chem. Commun. (1999) 1737
14. Organ M.G., Dragan V., Miller M., Froese R.D.J., and Goddard J.D. J. Org. Chem. 65 (2000) 3666
15. Brengel G.P., Rithner C., and Meyers A.I. J. Org. Chem. 59 (1994) 5144
16. Groaning M.D., Brengel G.P., and Meyers A.I. Tetrahedron 57 (2001) 2635
17. Murphy W.S., and Neville D. Tetrahedron Lett. 38 (1997) 7933
18. Photochemical [2+2]-cycloaddition reaction of acrylate and acrylamide derivatives was reported, see:. Fature S., Blanc S.P., and Piva O. Tetrahedron Lett. 40 (1999) 6001
19. Fallis A.G. Acc. Chem. Res. 32 (1999) 464
20. Suzuki Y., Murata T., Takao K., and Tadano K. J. Synth. Org. Chem., Jpn. 60 (2002) 679
21. Chackalamannil S., Davies R.J., Wang Y., Asberom T., Doller D., Wong J., and Leon D. J. Org. Chem. 64 (1999) 1932
22. Jauch J. Angew. Chem., Int. Ed. 39 (2000) 2764
23. Padwa A., Brodney M.A., Dimitroff M., Liu B., and Wu T. J. Org. Chem. 66 (2001) 3119
24. Suzuki Y., Ohara A., Sugaya K., Takao K., and Tadano K. Tetrahedron 57 (2001) 7291
25. Wong L.S.-M., and Sherburn M.S. Org. Lett. 5 (2003) 3603
26. Inoue M., Sato T., and Hirama M. J. Am. Chem. Soc. 125 (2003) 10772
27. Reviews on the intramolecular Diels-Alder reaction:. Ciganek E. In: Dauben W.G. (Ed). Organic Reactions Vol. 32 (1984), John Wiley & Sons, New York 1-374
28. Craig D. Chem. Soc. Rev. 16 (1987) 187
29. Roush W.R. In: Curran D.P. (Ed). Advances in Cycliaddition Vol. 2 (1990), JAI Press, Greenwich, CT 91-146
30. Roush W.R. In: Trost B.M., and Fleming I. (Eds). Comprehensive Organic Synthesis Vol. 5 (1991), Pergamon Press, Oxford, UK 513-550
31. Boeckman Jr. R.K., and Demko D.M. J. Org. Chem. 47 (1982) 1789
32. Martin S.F., Williamson S.A., Gist R.P., and Smith K.M. J. Org. Chem. 48 (1983) 5170
33. Cain D., Pawar D.M., Stewart M., Billings Jr. H., and Noe E.A. J. Org. Chem. 66 (2001) 6092
34. Review on the conformation and stereoelectronic effect of ester compounds, see:. Deslongchamps P. Stereoelectric Effects in Organic Chemistry (1983), Pergamon Press, Oxford 54-100
35. Saito A., Ito H., and Taguchi T. Org. Lett. 4 (2002) 4619
36. Saito A., Yanai H., and Taguchi T. Tetrahedron 60 (2004) 12239
37. Saito A., Yanai H., Sakamoto W., Takahashi K., and Taguchi T. J. Fluorine Chem. 126 (2005) 709
38. Example of intermolecular Diel-Alder reaction:. Saito A., Yanai H., and Taguchi T. Tetrahedron Lett. 45 (2004) 9439
39. Ooi T., Ohmatsu K., Ishii H., Saito A., and Maruoka K. Tetrahedron Lett. 45 (2004) 9315
40. Structures of the crystalline compounds 2b, 2c, and 2e were determined by their X-ray analyses, and the relative stereochemistries of compounds 2a, 2d, 2g, and 2h were determined by the NOESY spectra data. Crystallographic data have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication Nos. CCDC 604006 (2b), 604007 (2c), and 607008 (2e). These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.