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RESEARCH PRODUCT
Synthesis and application of new iminopyridine ligands in the enantioselective palladium-catalyzed allylic alkylation
Barbara SechiJosé R. PedroSalvatore BaldinoGiorgio ChelucciGonzalo BlayMaurizio Solinassubject
Steric effectsAllylic rearrangementChemistryProcess Chemistry and TechnologyIminopyridine ligandsEnantioselective synthesischemistry.chemical_elementQuímicaDimethyl malonateMedicinal chemistryAllylic substitutionPalladium catalysisCatalysisCatalysischemistry.chemical_compoundTsuji–Trost reactionOrganic chemistryEnantioselective catalysisPhysical and Theoretical ChemistryPalladiumdescription
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 Elsevier B.V.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2014-04-01 |