Organocatalytic Enantio- and Diastereoselective 1,3-Dipolar Cycloaddition between Alanine-Derived Ketonitrones and E-Crotonaldehyde: Efficiency and Full Stereochemical Study - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Tetrahedron: Asymmetry Année : 2012

Organocatalytic Enantio- and Diastereoselective 1,3-Dipolar Cycloaddition between Alanine-Derived Ketonitrones and E-Crotonaldehyde: Efficiency and Full Stereochemical Study

Résumé

Highly enantio- and exo-selective 1,3-dipolar cycloadditions of alanine-derived ketonitrones to E-crotonaldehyde could be realized in a good yield by the use of a chiral imidazolidinone salt without the addition of water. The origin of the stereoselectivity in the reaction was discussed and the absolute configuration of the cycloadduct determined unambiguously.

Domaines

Chimie organique

Dates et versions

hal-00761295 , version 1 (05-12-2012)

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Citer

Khalid B. Selim, Anne Beauchard, Jérôme Lhoste, Arnaud Martel, Mathieu Y. Laurent, et al.. Organocatalytic Enantio- and Diastereoselective 1,3-Dipolar Cycloaddition between Alanine-Derived Ketonitrones and E-Crotonaldehyde: Efficiency and Full Stereochemical Study. Tetrahedron: Asymmetry, 2012, 23 (24), pp.1670-1677. ⟨10.1016/j.tetasy.2012.11.010⟩. ⟨hal-00761295⟩
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