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Induction of axial dissymmetry into the 1,1′-binaphthyl bond via an intramolecular ullmann coupling reaction
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1980
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Cross-coupling ReactionEnantioselective SynthesisIntramolecular UllmannEngineeringAxial DissymmetryOrganic ChemistryIntramolecular Ullmann CouplingStereoselective SynthesisChemistrySupramolecular ChemistryComplete DiastereoselectivityAsymmetric Catalysis1,1′-Binaphthyl BondBiophysicsBiomolecular Engineering
Intramolecular Ullmann coupling of (S)-2,2′-bis-(1-bromo-2-naphthylcarbonyloxy)-1,1′-binaphthyl [(S)-(1)] induced axial dissymmetry of the S-configuration into the newly formed 1,1′-binaphthyl linkage affording (SS)-tetranaphtho[2,1-b; 1,2-d; 2,1-h; 1,2-j][1,6]dioxacyclododecene-11,26-dione [(SS)-(2)] with virtually complete diastereoselectivity.