Enantioselective diels-alder reactions of chiral racemic acyclic dienes with (SS)-2-(p-tolylsulfinyl)-1,4-naphthoquinone

Tetrahedron Asymmetry

Volumn 9, Issue 17, 1998, Pages 2965-2969

  Carreño, M Carmen ^a   García Cerrada, Susana ^a   Urbano, Antonio ^a   Di Vitta, Claudio ^a  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

1,4 NAPHTHOQUINONE DERIVATIVE; ALKADIENE;

ARTICLE; CHEMICAL REACTION KINETICS; CHIRALITY; CYCLIZATION; DRUG SYNTHESIS; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 0344936078     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(98)00323-1     Document Type: Article

References (40)

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22. For an overview of our work, see: (a) Carreño, M. C. Chem. Rev. 1995, 95, 1717-1760. For more recent references, see: (b) Carreño, M. C.; García Ruano, J. L.; Toledo, M. A.; Urbano, A.; Remor, C. Z.; Stefani, V.; Fischer, J. J. Org. Chem. 1996, 61, 503-509. (c) Carreño, M. C.; García Ruano, J. L.; Urbano, A.; Hoyos, M. A. J. Org. Chem. 1996, 61, 2980-2985. (d) Carreño, M. C.; García Ruano, J. L.; Urbano, A.; López-Solera, M. I. J. Org. Chem. 1997, 62, 976-981. (e) Carreño, M. C.; García Ruano, J. L.; Remor, C. Z.; Urbano, A.; Fischer, J. Tetrahedron Lett. 1997, 38, 9077-9080.
23. For an overview of our work, see: (a) Carreño, M. C. Chem. Rev. 1995, 95, 1717-1760. For more recent references, see: (b) Carreño, M. C.; García Ruano, J. L.; Toledo, M. A.; Urbano, A.; Remor, C. Z.; Stefani, V.; Fischer, J. J. Org. Chem. 1996, 61, 503-509. (c) Carreño, M. C.; García Ruano, J. L.; Urbano, A.; Hoyos, M. A. J. Org. Chem. 1996, 61, 2980-2985. (d) Carreño, M. C.; García Ruano, J. L.; Urbano, A.; López-Solera, M. I. J. Org. Chem. 1997, 62, 976-981. (e) Carreño, M. C.; García Ruano, J. L.; Remor, C. Z.; Urbano, A.; Fischer, J. Tetrahedron Lett. 1997, 38, 9077-9080.
24. For an overview of our work, see: (a) Carreño, M. C. Chem. Rev. 1995, 95, 1717-1760. For more recent references, see: (b) Carreño, M. C.; García Ruano, J. L.; Toledo, M. A.; Urbano, A.; Remor, C. Z.; Stefani, V.; Fischer, J. J. Org. Chem. 1996, 61, 503-509. (c) Carreño, M. C.; García Ruano, J. L.; Urbano, A.; Hoyos, M. A. J. Org. Chem. 1996, 61, 2980-2985. (d) Carreño, M. C.; García Ruano, J. L.; Urbano, A.; López-Solera, M. I. J. Org. Chem. 1997, 62, 976-981. (e) Carreño, M. C.; García Ruano, J. L.; Remor, C. Z.; Urbano, A.; Fischer, J. Tetrahedron Lett. 1997, 38, 9077-9080.
25. For an overview of our work, see: (a) Carreño, M. C. Chem. Rev. 1995, 95, 1717-1760. For more recent references, see: (b) Carreño, M. C.; García Ruano, J. L.; Toledo, M. A.; Urbano, A.; Remor, C. Z.; Stefani, V.; Fischer, J. J. Org. Chem. 1996, 61, 503-509. (c) Carreño, M. C.; García Ruano, J. L.; Urbano, A.; Hoyos, M. A. J. Org. Chem. 1996, 61, 2980-2985. (d) Carreño, M. C.; García Ruano, J. L.; Urbano, A.; López-Solera, M. I. J. Org. Chem. 1997, 62, 976-981. (e) Carreño, M. C.; García Ruano, J. L.; Remor, C. Z.; Urbano, A.; Fischer, J. Tetrahedron Lett. 1997, 38, 9077-9080.
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27. Carreño, M. C.; García Ruano, J. L.; Urbano, A. Synthesis 1992, 651-653.
28. 3) spectral data.
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33. Configurational assignments of derivatives 4a-f and 5a-f were established from NOE experiments.
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35. The racemic compounds necessary for such evaluation were prepared from the corresponding racemic sulfinylquinone (±)-1 (see Ref. 7).
36. We follow Franck's lead in utilizing this nomenclature, see: Ref. 4a, ftnt 5. See also, Seebach, D.; Prelog, V. Angew. Chem., Int. Ed. Engl. 1982, 21, 654-660.
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39. The discussion is focused on methyl substituted dienes 2a-c. Although the stereochemical descriptor changes from R=Me to R=Ph, the relative stability of the transition states is similar in both cases.
40. For phenyl substituted dienes 2d-f, the (S) enantiomer reacts faster.