Asymmetric Michael addition of acetone to β-nitrostyrenes catalyzed by novel organocatalysts derived from D-isomannide or L-isoidide - Institut des Molécules et Matériaux du Mans Accéder directement au contenu
Article Dans Une Revue ARKIVOC - Online Journal of Organic Chemistry Année : 2013

Asymmetric Michael addition of acetone to β-nitrostyrenes catalyzed by novel organocatalysts derived from D-isomannide or L-isoidide

Résumé

Novel bifunctional organocatalysts were prepared from D-isomannide or L-isoidide in three steps. These catalysts were then evaluated in the asymmetric Michael addition of acetone to trans--nitrostyrenes. Although moderate enantioselectivities were observed, this study has highlighted that a simple chiral primary diamine can catalyze this reaction. Furthermore, the reaction was also performed with an isomannide-derived diimine which was transformed in situ into the active catalyst under acidic conditions leading to the best enantioselectivity.

Dates et versions

hal-02143321 , version 1 (29-05-2019)

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Citer

Ling-Yan Chen, Stéphane Guillarme, Andrew Whiting, Christine Saluzzo. Asymmetric Michael addition of acetone to β-nitrostyrenes catalyzed by novel organocatalysts derived from D-isomannide or L-isoidide. ARKIVOC - Online Journal of Organic Chemistry, 2013, 2014 (4), pp.215. ⟨10.3998/ark.5550190.p008.429⟩. ⟨hal-02143321⟩
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