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Asymmetric Synthesis of Axially Chiral Benzamides and Anilides by Enantiotopic Lithiation of Prochiral Arene Chromium Complexes
journal contribution
posted on 2002-02-13, 00:00 authored by Hiroshige Koide, Takeshi Hata, Motokazu UemuraAxially chiral benzamides and anilides were prepared by enantiotopic lithiation at the distinguished
benzylic methyl of prochiral tricarbonylchromium complexes of N,N-diethyl 2,6-dimethylbenzamide
(1) and N-methyl-N-acyl 2,6-dimethylaniline (14 and 21) with a chiral lithium amide base followed
by electrophilic substitution in good yields with high optical purity. The resulting axially chiral
chromium-complexed benzamides and anilides were oxidized under air to give chromium-free axially
chiral benzamides and anilides in an enantiomerically active form without axial bond rotation at
room temperature.
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Axially Chiral Benzamideschiral lithium amide basechiral benzamidesbenzylic methylanilideprochiral tricarbonylchromium complexeselectrophilic substitutionenantiotopic lithiationAsymmetric Synthesisbond rotationProchiral Arene Chromium Complexes Axially chiral benzamidesEnantiotopic Lithiationroom temperature
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