Diels-Alder reaction of optically active (E)-γ-keto-α,β- unsaturated p-tolylsulfoxides with cyclopentadiene

Tetrahedron

Volumn 60, Issue 4, 2004, Pages 871-875

  Ordóñez, Mario ^a   De La Rosa, Victor Guerrero ^b   Alcudia, Felipe ^b   Llera, José Manuel ^b  

^a CENTRO DE INVESTIGACIONES QUÍMICAS   (Mexico)

^b UNIVERSITY OF SEVILLE   (Spain)

Author keywords

(E) Keto , unsaturated p tolylsulphoxides; Diels Alder reactions

Indexed keywords

ACRYLIC ACID DERIVATIVE; CARBONYL DERIVATIVE; CYCLOPENTADIENE DERIVATIVE; LEWIS ACID; SULFOXIDE;

ARTICLE; CATALYST; DIASTEREOISOMER; DIELS ALDER REACTION; ENANTIOMER; PRIORITY JOURNAL; STEREOCHEMISTRY;

BETULACEAE;

EID: 18544397932     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2003.11.047     Document Type: Article

References (32)

1. Fernández I., Khiar N. Chem. Rev. 103:2003;3651.
2. Khiar N., Fernández I., Alcudia A., Alcudia F. Rayner C.M. Advances in sulfur chemistry 2. 2000;57 JAI, Stanford, CT. Chapter 3.
3. García-Ruano J.L., Cid B. Page P.C.B. Topics in current chemistry. Vol. 204:1999;1-126 Springer, Berlin.
4. Page P.C.B. Organosulfur chemistry, synthetic and stereochemical aspects. Vol. 2:1998;Academic, London.
5. Aversa M.C., Barattucci A., Bonaccorsi P., Giannetto P. Tetrahedron: Asymmetry. 8:1997;1339.
6. Rayner C.M. Contemp. Org. Synth. 3:1996;499.
7. Carreño C.M. Chem. Rev. 95:1995;1717.
8. Metzner P., Thuillier A. Sulfur reagents in organic synthesis. 1994;Academic, London.
9. Walker A.J. Tetrahedron: Asymmetry. 3:1992;961.
10. Solladié G. Trost B.M., Fleming I. Comprehensive organic synthesis. Vol. 6:1991;133 Pergamon, Oxford.
11. Patai S., Rappoport Z., Stirling C.J.M. The chemistry of sulfones and sulfoxides. 1988;Wiley, New York.
12. Maignan C., Raphael R.A. Tetrahedron. 39:1983;3245.
13. Guessous A., Rouessac F., Maignan C. Bull. Soc. Chim. Fr. 1986;837.
14. De Lucchi O., Lucchini V., Marchioro C., Valle G., Modena G. J. Org. Chem. 51:1986;1457.
15. Fuji K., Tanaka K., Abe H., Matsumoto K., Harayama T., Ikeda A., Taga T., Miwa Y., Node M. J. Org. Chem. 59:1994;2221.
16. López R., Carretero J.C. Tetrahedron: Asymmetry. 2:1991;93.
17. Arai Y., Kuwayama S., Takeuchi Y., Koizumi T., Masuda T., Masaki Y. Synth. Commun. 16:1986;233.
18. De Lucchi O., Fabbri D., Lucchini V. Synlett. 1991;565.
19. Aggarwal V.N., Lightower M., Lindell S.D. Synlett. 1992;730.
20. Katagiri N., Ise S., Watanabe N., Kaneko C. Chem. Pharm. Bull. 38:1990;3242.
21. Carretero J.C., García-Ruano J.L., Martín-Cabrejas L.M. Tetrahedron: Asymmetry. 8:1997;409.
22. García-Ruano J.L., Alemparte C., Martín-Castro A.M., Adams H., Rodríguez-Ramos J.H. J. Org. Chem. 65:2000;7938.
23. García-Ruano J.L., Gamboa A.E., Martín-Castro A.M., Rodríguez J.H., López-Solera M.I. J. Org. Chem. 63:1998;3324.
24. See: Arai Y., Koizumi T. Sulfur Rep. 15:1993;41. and references therein.
25. Guerrero-de la Rosa V., Ordóñez M., Alcudia F., Llera J.M. Tetrahedron Lett. 36:1995;4889.
26. Brimble M.A., Davis R.D. Tetrahedron. 41:1985;4965.
27. Proust S.M., Ridley D.D. Aust. J. Chem. 37:1984;1677.
28. Koizumi T., Hakamada I., Yoshii E. Tetrahedron Lett. 25:1984;87.
29. Carreño M.C., García-Ruano J.L., Remor C.Z., Urbano A. Tetrahedron: Asymmetry. 11:2000;4279. and references cited therein.
30. García-Ruano J.L., Esteban Gamboa A., Martín-Castro A.M., Rodríguez-Ramos J.H., Lopez-Solera M.I. J. Org. Chem. 63:1998;3324.
31. Still W.C., Kahn M., Mitra A. J. Org. Chem. 43:1978;2923.
32. Brown H.C. Organic synthesis via boranes. 1975;Wiley, New York. p 256.