Journal of the American Chemical Society · 2017 · 10 citations · 39 references
Natural SciencesChemistryCatalysisOrganic ChemistryOrganometallic ChemistryChiral SeparationCoordination ChemistryCross-coupling ReactionsHeterocycle SynthesisOrganometallic SynthesisReductive EliminationAsymmetric C-c Bond FormationAsymmetric Heterocycle SynthesisBimetallic Reductive EliminationChiral Product SynthesisEnantioselective Reductive EliminationEnantioselective SynthesisStereoselective Cross-couplingThermal Reductive Elimination
A method is described for the joining of two α-lithiated C(sp 3 ) stereocenters efficiently and with retention of configuration. The key step involves the effective removal of two electrons from a chiral organocuprate R 2 CuLi, by i -propyl 2,4-dinitrobenzoate to form a Cu(III) complex that undergoes at −90 °C accelerated reductive elimination enantioselectively and exclusively without the formation of free radicals.
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