Enantioselective Michael Addition of Dimethyl Malonate to (E)-β- Nitrostyrenes Catalyzed by Cinchona Alkaloids Under Solvent-Free Condition

Francesco      Fringuelli; Luca      Castrica; Ferdinando      Pizzo; Luigi      Vaccaro

doi:10.2174/157017808786857499

Abstract

Under solvent-free condition the addition of dimethyl malonate (1) to (E)-β-nitrostyrenes 2a-j proceeds smoothly in the presence of 2.5 mol% of 6-hydroxy cinchonine (QD-OH) and equimolar amounts of reagents at 30 °C. The corresponding products 3a-j are obtained with satisfactory enantiomeric excesses (68-88%) and high yields (70- 92%).

Keywords: Nitroalkenes, organocatalysts, solvent-free condition, Michael addition

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Letters in Organic Chemistry

Title: Enantioselective Michael Addition of Dimethyl Malonate to (E)-β- Nitrostyrenes Catalyzed by Cinchona Alkaloids Under Solvent-Free Condition

Volume: 5 Issue: 8

Author(s): Francesco Fringuelli, Luca Castrica, Ferdinando Pizzo and Luigi Vaccaro

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Keywords: Nitroalkenes, organocatalysts, solvent-free condition, Michael addition

Abstract: Under solvent-free condition the addition of dimethyl malonate (1) to (E)-β-nitrostyrenes 2a-j proceeds smoothly in the presence of 2.5 mol% of 6-hydroxy cinchonine (QD-OH) and equimolar amounts of reagents at 30 °C. The corresponding products 3a-j are obtained with satisfactory enantiomeric excesses (68-88%) and high yields (70- 92%).

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Fringuelli Francesco, Castrica Luca, Pizzo Ferdinando and Vaccaro Luigi, Enantioselective Michael Addition of Dimethyl Malonate to (E)-β- Nitrostyrenes Catalyzed by Cinchona Alkaloids Under Solvent-Free Condition, Letters in Organic Chemistry 2008; 5 (8) . https://dx.doi.org/10.2174/157017808786857499