1,3-Dipolar Cycloaddition of Hydrazones with ?-Oxo-ketenes: A Three-Component Stereoselective Entry to Pyrazolidinones and an Original Class of Spirooxindoles - Aix-Marseille Université Accéder directement au contenu
Article Dans Une Revue Organic Letters Année : 2011

1,3-Dipolar Cycloaddition of Hydrazones with ?-Oxo-ketenes: A Three-Component Stereoselective Entry to Pyrazolidinones and an Original Class of Spirooxindoles

Marc Presset
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Marie Hamann
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Yoann Coquerel
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Jean Rodriguez
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Résumé

Stereodefined monocyclic, spirobicyclic, and bis-spirotricyclic pyrazolidin-3-ones can be prepared efficiently by a three-component reaction involving a 1,3-dipolar cycloaddition of azomethine imines obtained from hydrazones with alpha-oxo-ketene dipolarophiles generated in situ. The reaction allows the creation of four covalent bonds and two contiguous chiral quaternary centers with excellent diastereoselectivity in a single catalyst/additive-free, highly atom-economical transformation. From a fundamental point of view, the reaction introduces alpha-oxo-ketenes as effective dipolarophiles in 1,3-dipolar cycloadditions.
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Dates et versions

hal-00677642 , version 1 (09-03-2012)

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Citer

Marc Presset, Marie Hamann, Yoann Coquerel, Jean Rodriguez. 1,3-Dipolar Cycloaddition of Hydrazones with ?-Oxo-ketenes: A Three-Component Stereoselective Entry to Pyrazolidinones and an Original Class of Spirooxindoles. Organic Letters, 2011, 13, pp.4124-4127. ⟨10.1021/ol2016669⟩. ⟨hal-00677642⟩
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