New strategies for intramolecular annulations: Intramolecular additions of silyloxycyclopropane-derived anions; application to hydrindenone syntheses

Journal of the Brazilian Chemical Society

Volumn 9, Issue 4, 1998, Pages 345-356

  Marino, J P ^a   Stengel, Peter J ^a   Simonelli, Fabio ^b   Ferreira, J Tércio B ^c  

^a UNIVERSITY OF MICHIGAN   (United States)

^b FEDERAL UNIVERSITY OF PARANÁ   (Brazil)

^c FEDERAL UNIVERSITY OF SÃO CARLOS   (Brazil)

Author keywords

Hydrindenone syntheses; Silyloxycyclopropane derived anions

Indexed keywords

EID: 0032333554     PISSN: 01035053     EISSN: None     Source Type: Journal    
DOI: 10.1590/S0103-50531998000400007     Document Type: Article

References (29)

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21. For the analogous coupling of vinyl triflates see: a) Scott, W.J.; Crisp, G.T.; Stille, J.K. J. Am. Chem. Soc. 1984, 106, 4630; b) Scott, W.J.; Stille, J.K. J. Am. Chem. Soc. 1986, 108, 3033; c) Stille J.K.; Tanaka, M. J. Am. Chem. Soc. 1987, 109, 3785; d) Echavarren, A.M.; Stille, J.K. J. Am. Chem. Soc. 1987, 109, 5478.
22. For the analogous coupling of vinyl triflates see: a) Scott, W.J.; Crisp, G.T.; Stille, J.K. J. Am. Chem. Soc. 1984, 106, 4630; b) Scott, W.J.; Stille, J.K. J. Am. Chem. Soc. 1986, 108, 3033; c) Stille J.K.; Tanaka, M. J. Am. Chem. Soc. 1987, 109, 3785; d) Echavarren, A.M.; Stille, J.K. J. Am. Chem. Soc. 1987, 109, 5478.
23. For the analogous coupling of vinyl triflates see: a) Scott, W.J.; Crisp, G.T.; Stille, J.K. J. Am. Chem. Soc. 1984, 106, 4630; b) Scott, W.J.; Stille, J.K. J. Am. Chem. Soc. 1986, 108, 3033; c) Stille J.K.; Tanaka, M. J. Am. Chem. Soc. 1987, 109, 3785; d) Echavarren, A.M.; Stille, J.K. J. Am. Chem. Soc. 1987, 109, 5478.
24. For the analogous coupling of vinyl triflates see: a) Scott, W.J.; Crisp, G.T.; Stille, J.K. J. Am. Chem. Soc. 1984, 106, 4630; b) Scott, W.J.; Stille, J.K. J. Am. Chem. Soc. 1986, 108, 3033; c) Stille J.K.; Tanaka, M. J. Am. Chem. Soc. 1987, 109, 3785; d) Echavarren, A.M.; Stille, J.K. J. Am. Chem. Soc. 1987, 109, 5478.
25. These compounds were readily prepared by LDA deprotonation of methylphenyl sulfone of dimethyl sulfone in THF at -20°C, followed by the addition of DMF (see: Kozerski, L. et al. Tetrahedron 1986, 42, 1469 for the analogous reaction with methylphenyl sulfoxide). Treatment of the filtered solid with 1.05 equivalents of TsCl in THF gave the trans-2-tosyl-vinyl sulfones, separable from the minor cis isomer by flash chromatography.
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27. Compounds 20 and 21 were eventually obtained in a pure state by Fabio Simonelli and NMR analyses were done on these samples. Unpublished results.
28. The stereochemistry of the sulfone side chain is expected to be pseudoaxial based on the A-strain model for cyclohexene systems. See: Johnson, F. Chem. Rev. 1968, 68, 375.
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