On the mechanism and diastereoselectivity of 2,3-dihydrobenzofuran formation from sulfinylbenzoquinones and 2-trimethylsilyloxyfuran

Tetrahedron Asymmetry

Volumn 10, Issue 22, 1999, Pages 4357-4367

  Carreño, M Carmen ^a   García Ruano, José L ^a   Urbano, Antonio ^a   Remor, Cynthia Z ^a,b   Arroyo, Yolanda ^a  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

^b FEDERAL UNIVERSITY OF RIO GRANDE DO SUL   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOQUINONE DERIVATIVE; DIHYDROBENZOFURAN DERIVATIVE;

ARTICLE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; DIASTEREOISOMER; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033370550     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(99)00460-7     Document Type: Article

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19. 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. Carreño, M. C.; Urbano, A.; Fischer, J. Angew. Chem., Int. Ed. Engl. 1997, 36, 1621-1623. (d) Carreño, M. C.; Urbano, A.; Di Vitta, C. J. Org. Chem. 1998, 63, 8320-8330. (e) Carreño, M. C.; Hérnandez-Sánchez, R.; Mahugo, J.; Urbano, A. J. Org. Chem. 1999, 64, 1387-1390. (f) Carreño, M. C.; Urbano, A.; Di Vitta, C. Chem. Commun. 1999, 817-818.
20. 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. Carreño, M. C.; Urbano, A.; Fischer, J. Angew. Chem., Int. Ed. Engl. 1997, 36, 1621-1623. (d) Carreño, M. C.; Urbano, A.; Di Vitta, C. J. Org. Chem. 1998, 63, 8320-8330. (e) Carreño, M. C.; Hérnandez-Sánchez, R.; Mahugo, J.; Urbano, A. J. Org. Chem. 1999, 64, 1387-1390. (f) Carreño, M. C.; Urbano, A.; Di Vitta, C. Chem. Commun. 1999, 817-818.
21. 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. Carreño, M. C.; Urbano, A.; Fischer, J. Angew. Chem., Int. Ed. Engl. 1997, 36, 1621-1623. Carreño, M. C.; Urbano, A.; Di Vitta, C. J. Org. Chem. 1998, 63, 8320-8330. (e) Carreño, M. C.; Hérnandez-Sánchez, R.; Mahugo, J.; Urbano, A. J. Org. Chem. 1999, 64, 1387-1390. (f) Carreño, M. C.; Urbano, A.; Di Vitta, C. Chem. Commun. 1999, 817-818.
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. Carreño, M. C.; Urbano, A.; Fischer, J. Angew. Chem., Int. Ed. Engl. 1997, 36, 1621-1623. (d) Carreño, M. C.; Urbano, A.; Di Vitta, C. J. Org. Chem. 1998, 63, 8320-8330. (e) Carreño, M. C.; Hérnandez-Sánchez, R.; Mahugo, J.; Urbano, A. J. Org. Chem. 1999, 64, 1387-1390. (f) Carreño, M. C.; Urbano, A.; Di Vitta, C. Chem. Commun. 1999, 817-818.
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31. The presence of this hydrogen bonding was evident from the 1H NMR spectra of 3b and 4b, where the phenolic proton appears very deshielded at 10.70 and 10.82 ppm, respectively.
32. 3 at 500 MHz.