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- W1969968017 abstract "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. Atropisomeric anilide products highly prefer to exist as the E-rotamer which has trans-disposed o-tert-butylphenyl group and carbonyl oxygen. The application of the present catalytic enantioselective N-arylation to an intramolecular version gives atropisomeric lactam derivatives with high optical purity (92−98% ee). The reaction of the lithium enolate prepared from the atropisomeric anilide and lactam products with various alkyl halides gives α-alkylated products with high diastereoselectivity (diastereomer ratio = 13:1 to 46:1)." @default.
- W1969968017 created "2016-06-24" @default.
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- W1969968017 date "2006-09-07" @default.
- W1969968017 modified "2023-10-18" @default.
- W1969968017 title "Highly Enantioselective Synthesis of Atropisomeric Anilide Derivatives through Catalytic Asymmetric N-Arylation: Conformational Analysis and Application to Asymmetric Enolate Chemistry" @default.
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- W1969968017 doi "https://doi.org/10.1021/ja064026n" @default.
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