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Letters in Organic Chemistry

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

DOI: 10.2174/157017808786857499

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

Page: [602 - 606] Pages: 5

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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