6533b853fe1ef96bd12ad5a0

RESEARCH PRODUCT

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

M. Carmen MuñozMiguel EspinosaJorge HerreraGonzalo BlayLuz CardonaJosé R. Pedro

subject

Trifluoromethyl010405 organic chemistryChemistryOrganic ChemistryEnantioselective synthesischemistry.chemical_elementOptically active010402 general chemistry01 natural sciencesBiochemistryCopper0104 chemical sciencesStereocenterchemistry.chemical_compoundCatàlisiMethyl malonateFISICA APLICADAMichael reactionOrganic chemistryPhysical and Theoretical ChemistryQuímica orgànicaConjugate

description

[EN] Copper triflate-BOX complexes catalyse the enantioselective conjugate addition of methyl malonate to beta-trifluoromethyl-alpha,beta-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 beta-trifluoromethyl delta-amino esters and optically active trifluoromethyl piperidones.

https://doi.org/10.1039/c7ob00595d