Copper-catalysed enantioselective Michael addition of malonic esters to β-trifluoromethyl-α, β-unsaturated imines. Issue 18 (13th April 2017)

• Record Type: Journal Article
• Authors: Espinosa, Miguel; Herrera, Jorge; Blay, Gonzalo; Cardona, Luz; Muñoz, M. Carmen; Pedro, José R.
• Is Part Of: Organic & biomolecular chemistry. Volume 15:Issue 18(2017)
• Page Start: 3849
• Page End: 3853
• Publication Date: 2017-04-13
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c7ob00595d
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : A diastereo- and enantioselective Michael addition of methyl malonate to β-trifluoromethyl unsaturated imines is presented. 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.