Search results for "Methyl malonate"
showing 4 items of 4 documents
CaCl2, Bisoxazoline, and Malonate: A Protocol for an Asymmetric Michael Reaction
2015
A mild protocol for the asymmetric Michael addition of dimethyl malonate to various α,β-unsaturated carbonyl compounds was developed. The salient feature of this methodology is that a cheap and environmentally friendly Lewis acid, CaCl2, was used as a catalyst. An aminoindanol- and pyridine-derived ligand provided in the presence of CaCl2 Michael adducts in moderate to high enantioselectivities. The scope of the reaction was demonstrated.
Synthesis and application of new iminopyridine ligands in the enantioselective palladium-catalyzed allylic alkylation
2014
A variety of iminopyridines were obtained by condensation of chiral amines with pyridine-2-carboxaldehyde and quinoline-8-carbaldehyde, or of aminoalkylpyridine derivatives with chiral ketones. These ligands were assessed in the enantioselective palladium catalyzed allylic substitution of 1,3-diphenylprop-2-enyl acetate with dimethyl malonate affording the product dimethyl 1,3-diphenylprop-2-enylmalonate in good yields and moderate enantioselectivities (up to 62% ee). Catalytic activity and enantioselectivity were found to be highly dependent upon the steric properties of the ligands. The best enantioselectivity (62% ee) was obtained by an iminopyridine based on a camphane skeleton. © 2014 …
Copper-catalysed enantioselective Michael addition of malonic esters to β-trifluoromethyl-α,β-unsaturated imines
2017
[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.
Dimethyl 2-(1-methyl-3-oxo-1,3-dihydroisobenzofuran-1-yl)malonate
2020
In this work we report a facile access to a 3,3-disubstituted isobenzofuranone by tandem addition/cyclization reaction to methyl 2-acetylbenzoate in the presence of dimethyl malonate, under basic conditions.