Journal of the American Chemical Society · 2016 · 51 citations · 32 references
Natural SciencesChemistryCatalysisOrganic ChemistryOrganometallic ChemistryCatalyst DesignCatalytic MaterialsCatalytic MechanismsDiversity-oriented SynthesisOrganic SynthesisRedox CatalysisC - H Bond FunctionalizationC-h ActivationCatalyst Structure - Activity RelationshipsEnantioselective Catalyst DesignHeterocycle FunctionalizationSubstrate ScopeSubstrate Scope ExpansionTransition-metal-catalyzed Functionalization
Enantioselective C-H functionalization of relatively electron-deficient methyl sites was achieved with the combination of 2,2,2-trichloroethyl aryldiazoacetates and tetrakis(triarylcyclopropanecarboxylate) dirhodium catalysts. The substrate scope of the transformation was relatively broad, and C-H functionalization products were furnished with excellent levels of enantioselectivity. As a strategic reaction, crotonate derivatives give 1,6-dicarbonyl compounds, which are useful for further diversification.
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