Asymmetric Diels-Alder reactions of 5-substituted and 5,6-disubstituted (S)-2-(p-tolylsulfinyl)-1,4-benzoquinones with cyclopentadiene and trans- piperylene

Tetrahedron Asymmetry

Volumn 10, Issue 6, 1999, Pages 1119-1128

  Carreńo, M Carmen ^a   García Ruano, José L ^a   Lafuente, Celia ^a   Toledo, Miguel A ^a  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOQUINONE DERIVATIVE; CYCLOPENTADIENE DERIVATIVE; ZINC BROMIDE;

ARTICLE; CHEMICAL INTERACTION; CHEMICAL REACTION; CHEMICAL STRUCTURE; MOLECULAR DYNAMICS; MOLECULAR INTERACTION; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0033605529     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(99)00094-4     Document Type: Article

References (24)

1. For general reviews on Asymmetric Diels-Alder reactions see: (a) Oppolzer, W. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I.; Paquette, L. A., Eds; Pergamon: Oxford, 1991; Vol. 5, pp. 315-399.
2. (b) Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1984, 23, 876-889.
3. (c) Taschner, M. J. In Asymmetric Diels-Alder Reactions; Taschner, M. J., Ed.; Jai Press: Greenwich, 1989; Vol. 1, pp. 1-101.
4. For recent examples see: Brimble, M. A.; Duncalf, L. J.; Reid, D. C. W.; Roberts, T. R. Tetrahedron 1998, 54, 5363.
5. (a) Carreño, M. C.; García Ruano, J. L.; Urbano, A. Tetrahedron Lett. 1989, 30, 4003.
6. (b) Carreño, M. C.; García Ruano, J. L.; Mata, J. M.; Urbano, A. Tetrahedron 1991, 47, 605.
7. (c) Carreño, M. C.; García Ruano, J. L.; Urbano, A. Synthesis 1992, 651.
8. (a) Carreño, M. C.; García Ruano, J. L.; Toledo, M. A.; Urbano, A.; Remor, C. Z.; Stefani, V.; Fischer, J. J. Org. Chem. 1996, 61, 503.
9. (b) Carreño, M. C.; García Ruano, J. L.; Urbano, A.; Hoyos, M. A. J. Org. Chem. 1996, 61, 2980.
10. (c) Carreño, M. C.; García Ruano, J. L.; Urbano, A. Tetrahedron Lett. 1994, 35, 3789.
11. (d) Carreño, M. C.; García Ruano, J. L.; Urbano, A. J. Org. Chem. 1996, 61, 6136.
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14. (a) Carreńo, M. C.; Urbano, A.; Fischer, J. Angew. Chem., Int. Ed. Engl. 1997, 36, 1621.
15. (b) Carreño, M. C.; García Ruano, J. L.; Remor, C. Z.; Urbano, A.; Fischer, J. Tetrahedron Lett. 1997, 38, 9077.
16. Thomson, R. H. In: Naturally Occurring Quinones IV. Recent Advances; Ed. Blackie Academic and Professional: Chapman and Hall: London, 1997.
17. (a) Andersen, K. K. Tetrahedron Lett. 1962, 93.
18. (b) Solladié, G.; Hutt, J.; Girardin, A. Synthesis 1987, 173.
19. Carreño, M. C.; García Ruano, J. L.; Toledo, M. A.; Urbano, A. Tetrahedron: Asymmetry 1997, 8, 913.
20. For a detailed discussion of a similar configurational assignment see Refs 3 and 4, and Carreño, M. C.; García Ruano, J. L.; Urbano, A.; López Solera, M. I. J. Org. Chem. 1997, 62, 976.
21. 3 which required the use of racemic 6 synthesised from racemic sulfinylquinones 3.
22. p-Toluene sulfenic acid formed in the pyrolysis could act as a reducing agent in these reactions.
23. For an example of inversion of regioselectivity in the presence of a Lewis acid in Diels-Alder reactions of 8-hydroxy-2-(or 3)-p-tolylsulfinyl-1,4-naphthoquinone see: Boeckman Jr., R. K.; Dolak, T. M.; Culos, K. O. J. Am. Chem. Soc. 1978, 100, 7098.
24. A remote methoxy substituent has a strong influence on the orientation of cycloadditions of substituted 1,4-benzoquinones: Tou, J. S.; Reusch, W. J. Org. Chem. 1980, 45, 5012.