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À propos de : Highly Enantioselective Synthesis of Atropisomeric AnilideDerivatives through Catalytic Asymmetric N-Arylation: Conformational Analysis and Application to AsymmetricEnolate Chemistry        

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  • Highly Enantioselective Synthesis of Atropisomeric AnilideDerivatives through Catalytic Asymmetric N-Arylation: Conformational Analysis and Application to AsymmetricEnolate Chemistry
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  • In the presence of (R)-DTBM-SEGPHOS−Pd(OAc)2 catalyst, N-arylation (aromatic amination)of various o-tert-butylanilides with p-iodonitrobenzene proceeds with high enantioselectivity (88−96% ee)to give atropisomeric N-(p-nitrophenyl)anilides having an N−C chiral axis in good yields. Atropisomericanilide products highly prefer to exist as the E-rotamer which has trans-disposed o-tert-butylphenyl groupand carbonyl oxygen. The application of the present catalytic enantioselective N-arylation to an intramolecularversion gives atropisomeric lactam derivatives with high optical purity (92−98% ee). The reaction of thelithium enolate prepared from the atropisomeric anilide and lactam products with various alkyl halides givesα-alkylated products with high diastereoselectivity (diastereomer ratio = 13:1 to 46:1).
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