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Synlett 2000; 2000(4): 514-516
DOI: 10.1055/s-2000-6565
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First Asymmetric Synthesis of 3-Methyltetrahydroquinolin-4-ones from Anilines

Ivan L. Baraznenok* , Valentine G. Nenajdenko, Andrei V. Churakov, Pavel N. Nesterenko, Elizabeth S. Balenkova
  • *Department of Chemistry, Moscow State University, 119899 Moscow, Russia; Fax +7-(0 95)-9 32-88-46; E-mail: Nen@acylium.chem.msu.ru
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Publication Date:
31 December 2000 (online)

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Reaction of N-methacryloyl SMP-triflic anhydride complex (2) with secondary aromatic amines followed by hydrolysis gives enantiomerically enriched (up to 81% ee) tetrahydroquinolinones 4a-f in moderate yields. The absolute configuration of 4f was established by an X-ray structure determination.

asymmetric synthesis - triflic anhydride - iminium salts - tandem reactions - Michael additions

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