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Copper-catalysed enantioselective Michael addition of malonic esters to β-trifluoromethyl-α,β-unsaturated imines

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Abstract

Copper triflate-BOX complexes catalyse the enantioselective conjugate addition of methyl malonate to β-trifluoromethyl-α,β-unsaturated imines to give the corresponding enamines bearing a trifluoromethylated stereogenic centre with good yields, and diastereo- and enantioselectivities. The usefulness of the method has been shown with the synthesis of optically active β-trifluoromethyl δ-amino esters and optically active trifluoromethyl piperidones.

Graphical abstract: Copper-catalysed enantioselective Michael addition of malonic esters to β-trifluoromethyl-α,β-unsaturated imines

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Publication details

The article was received on 09 Mar 2017, accepted on 06 Apr 2017 and first published on 06 Apr 2017


Article type: Communication
DOI: 10.1039/C7OB00595D
Citation: Org. Biomol. Chem., 2017, Advance Article
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    Copper-catalysed enantioselective Michael addition of malonic esters to β-trifluoromethyl-α,β-unsaturated imines

    M. Espinosa, J. Herrera, G. Blay, L. Cardona, M. C. Muñoz and J. R. Pedro, Org. Biomol. Chem., 2017, Advance Article , DOI: 10.1039/C7OB00595D

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