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Synlett 2000; 2000(8): 1145-1147
DOI: 10.1055/s-2000-6765
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Synthesis of Axially Chiral Anilides by Enantioselective Desymmetrization of Tricarbonyl(N-Methyl, N-Aroyl 2,6-Dimethylaniline)Chromium Complexes

Takeshi Hata* , Hiroshige Koide, Motokazu Uemura
  • *Department of Chemistry, Faculty of Integrated Arts and Sciences, Osaka Prefecture University, Sakai, Osaka 599-8531, Japan; Fax+ 81 722 54 99 31; E-mail: uemura@ms.cias.osakafu-u.ac.jp
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Publication Date:
31 December 2000 (online)

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Axially chiral anilides were prepared in high optical purity by enantiotopic lithiation at the discriminated benzylic methyl of prochiral tricarbonylchromium-complexed N-methyl, N-o-methylbenzoyl 2,6-dimethylanilide with chiral lithium amide followed by electrophilic substitution.

arene complexes - atropisomerism - chiral amines - chromium - enantioselective lithiation