Influence of diene substitution on Diels-Alder reactions between vinyl dihydronaphthalenes and (SS)-2-(p-tolylsulfinyl)-1,4-benzoquinone

Journal of Organic Chemistry

Volumn 68, Issue 11, 2003, Pages 4315-4321

  Carreño, M Carmen ^a   García Cerrada, Susana ^a   Sanz Cuesta, M Jesús ^a   Urbano, Antonio ^a  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

DIELS-ALDER REACTION;

CHEMICAL BONDS; KETONES; NAPHTHALENE; STEREOCHEMISTRY;

SUBSTITUTION REACTIONS;

2 (2 ACETOXYVINYL) 8 TERT BUTYL 3,4 DIHYDRONAPHTHALENE; 2 (4 TOLYLSULFINYL) 1,4 BENZOQUINONE; ALKADIENE; BENZOQUINONE DERIVATIVE; NAPHTHALENE DERIVATIVE; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ARTICLE; CHEMICAL BOND; CHEMICAL STRUCTURE; CYCLOADDITION; DIELS ALDER REACTION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0038779429     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0342774     Document Type: Article

References (38)

1. Recent review: Cid, B.; García Ruano, J. L. Organosulfur Chemistry I. In Topics in Current Chemistry; Springer: Berlin, Germany, 1999, 204, 1-126.
2. Review: Aversa, M. C.; Barattucci, A.; Bonaccorsi, P.; Giannetto, P. Tetrahedron: Asymmetry 1997, 8, 1339-1367.
3. (a) Carreño, M. C.; García Ruano, J. L.; Urbano, A. Tetrahedron Lett. 1989, 30, 4003-4006.
4. (b) Carreño, M. C.; García Ruano, J. L.; Toledo, M. A.; Urbano, A. Tetrahedron Lett. 1994, 35, 9759-9762.
5. (c) Carreño, M. C.; García Ruano, J. L.; Toledo, M. A.; Urbano, A.; Remor, C. Z.; Stefani, V. J. Org. Chem. 1996, 61, 503-509.
6. (d) Carreño, M. C.; Mahugo, J.; Urbano, A. Tetrahedron Lett. 1997, 38, 3047-3050.
7. (e) Carreño, M. C.; García Ruano, J. L.; Remor, C. Z.; Urbano, A. Tetrahedron Lett. 1997, 38, 9077-9080.
8. (f) Carreño, M. C.; García Ruano, J. L.; Urbano, A.; Remor, C. Z.; Arroyo, Y. J. Org. Chem. 2000, 65, 453-458.
9. (g) Carreño, M. C.; Urbano, A. Tetrahedron Lett. 2000, 41, 4117-4121.
10. (h) Carreño, M. C.; García Ruano, J. L.; Remor, C. Z.; Urbano, A. Tetrahedron: Asymmetry 2000, 11, 4279-4296.
11. (a) Carreño, M. C.; García Ruano, J. L.; Urbano, A. J. Org. Chem. 1992, 57, 6870-6876.
12. (b) Carreño, M. C.; García Ruano, J. L.; Urbano, A. Tetrahedron Lett. 1994, 35, 3789-3792.
13. (c) Carreño, M. C.; García Ruano, J. L.; Urbano, A.; Hoyos, M. A. J. Org. Chem. 1996, 61, 2980-2985.
14. (d) Carreño, M. C.; García Ruano, J. L.; Urbano, A.; López-Solera, M. I. J. Org. Chem. 1997, 62, 976-981.
15. (e) Carreño, M. C.; García-Cerrada, S.; Urbano, A.; Di Vitta, C. Tetrahedron: Asymmetry 1998, 9, 2965-2969.
16. (f) Carreño, M. C.; Urbano, A.; Di Vitta, C. J. Org. Chem. 1998, 63, 8320-8330.
17. (g) Carreño, M. C.; García-Cerrada, S.; Urbano, A.; Di Vitta, C. J. Org. Chem. 2000, 65, 4355-4363.
18. (a) Carreño, M. C.; Urbano, A.; Fischer, J. Angew. Chem., Int. Ed. Engl. 1997, 36, 1621-1623.
19. (b) Carreño, M. C.; Urbano, A.; Di Vitta, C. Chem. Commun. 1999, 817818.
20. (c) Carreño, M. C.; Urbano, A.; Di Vitta, C. Chem. Eur. J. 2000, 6, 906-913.
21. (a) Carreño, M. C.; Hérnandez-Sánchez, R.; Mahugo, J.; Urbano, A. J. Org. Chem. 1999, 64, 1387-1390.
22. (b) Carreño, M. C.; García-Cerrada, S.; Urbano, A. J. Am. Chem. Soc. 2001, 123, 7929-7930.
23. (c) Carreño, M. C.; García-Cerrada, S.; Urbano, A. Chem. Commun. 2002, 1412-1413.
24. The tautomeric equilibrium existent in naphthazarin derivatives makes the system an ambident dienophile: Carreño, M. C.; García Ruano, J. L.; Urbano, A. Tetrahedron 1994, 50, 5013-5020.
25. Carreño, M. C.; Urbano, A. Unpublished results.
26. Carreño, M. C.; García-Cerrada, S.; Sanz-Cuesta, M. J.; Urbano, A. Chem. Commun. 2001, 1452-1453.
27. Kasatkin, A.; Nakagawa, T.; Okamoto, S.; Sato, F. J. Am. Chem. Soc. 1995, 117, 3881-3882.
28. Sodeoka, M.; Iimori, T.; Shibasaki, M. Chem. Pharm. Bull. 1991, 39, 323-327.
29. Carreño, M. C.; García Ruano, J. L.; Urbano, A. Synthesis 1992, 651-653.
30. (a) Tietze, L. F.; Schuffenhauer, A.; Schreiner, P. R. J. Am. Chem. Soc. 1998, 120, 7952-7958.
31. (b) Kahn, S. D.; Hehre, W. J. J. Am. Chem. Soc. 1987, 109, 663-666.
32. (c) Kahn, S. D.; Hehre, W. J. Tetrahedron Lett. 1986, 27, 6041-6044.
33. García Ruano, J. L.; Carreño, M. C.; Carretero, J. C.; Martín Cabrejas, L. M.; Urbano, A. Pure Appl. Chem. 1996, 68, 925-930.
34. Two or more substituents in the diene partner make a regiochemical prediction on the basis of FMO theory difficult: Kahn, S. D.; Hehre, W. J. J. Am. Chem. Soc. 1986, 108, 7381-7396.
35. Hansch, C.; Leo, A.; Taft, R. W. Chem. Rev. 1991, 91, 165-195.
36. Kamble, R. M.; Singh, V. K. Tetrahedron Lett. 2001, 42, 7525-7526.
37. Fleming, I. In Frontier Orbitals and Organic Reactions; John Wiley & Sons: London, UK, 1976.
38. Robiette, R.; Marchand-Brynaert, J.; Peeters, D. J. Org. Chem. 2002, 67, 6823-6826 and references therein.