Rhodium carbenoid mediated cyclisation of α-diazo-β-keto-δ-hydroxy- phenylsulfones

Tetrahedron Letters

Volumn 41, Issue 24, 2000, Pages 4773-4776

  Lacrampe, Fabienne ^a   Léost, Françoise ^a   Doutheau, Alain ^a  

^a UNIVERSITÉ DE LYON   (France)

Author keywords

Carbenoids; Diazo compounds; Furans; Insertion reactions; Sulfones

Indexed keywords

CARBENOID; RHODIUM COMPLEX; SULFONE DERIVATIVE; TETRAHYDROFURAN DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; REACTION ANALYSIS;

EID: 0343953365     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00724-3     Document Type: Article

References (30)

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2. Davies, M. J.; Moody, C. J.; Taylor, R. J. J. Chem. Soc., Perkin Trans. 1 1991, 1-7. For the cyclisation of γ-hydroxy α-diazo-β-sulfonylesters into 3-oxocephan dioxides, see: Crackett, P. H.; Sayer, P.; Stoodley, R. J.; Greengrass, C. W. J. Chem. Soc., Perkin Trans. 1 1991, 1235-1243.
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20. In the case of 7b the reaction mixture was refluxed for 1 h.
21. To the best of our knowledge 3-oxo-tetrahydrofurans bearing a sulfonyl group in C-2 position have not yet been described in the literature.
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25. The reduction of the mixture of the two diastereomers of 4c led to only two diastereomers of 10, among four possible. This result is in accordance with the well documented high cis diastereoselectivity of sodium borohydride reduction of β-ketosulfones. Since it was quite unlikely that the success of the chemistry planned to transform 10 into dihydrofuran derivatives, would significantly depend on the cis or trans relationship between the hydroxy-phenylsulfonyl moiety and the phenyl group, at this stage of our work we did not try to assign the stereochemistry of the major and of the minor diastereomer. We further used the former compound obtained in larger amount.
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30. Similar yields have been reported in the literature for sodium amalgam desulfonation of β-hydroxy sulfones leading to cyclopentene derivatives. For example, see: Gamble, M. P.; Gibbin, G. M. P.; Taylor, R. J. K. Synlett 1995, 779-780.