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Asymmetric Rhodium-Catalysed Addition of Arylboronic Acids to Acyclic Unsaturated Esters Containing a Basic γ-Amino Group
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2012
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Arylboronic AcidsSubstitution PatternsEngineeringNatural SciencesAryl Boronic AcidsDiversity-oriented SynthesisBasic γ-Amino GroupSubstituted β-Phenyl GroupOrganic ChemistryAsymmetric Rhodium-catalysed AdditionCatalysisOrganometallic CatalysisChemistryNatural Product SynthesisAsymmetric CatalysisSynthetic ChemistryEnantioselective SynthesisBiomolecular Engineering
Application of the Miyaura–Hayashi rhodium-catalysed addition of aryl boronic acids to acyclic unsaturated esters featuring basic centres to yield γ-amino butyric acids incorporating a substituted β-phenyl group is described. Unoptimised isolated yields and enantiomeric excesses vary from moderate to excellent, and the method tolerates a variety of substitution patterns and a range of functionality.