Abstract
Enantiomerically pure (S)-5,6,7,8-tetrahydroquinolin-8-ol [(S)-1] and (R)-8-acetoxy-5,6,7,8-tetrahydroquinoline [(R)-2] have been prepared by the lipase-catalyzed kinetic acetylation of racemic 5,6,7,8-tetrahydroquinolin-8-ol [(±)-1] in excellent chemical yields. The mesylation of (R)-1 followed by a substitution reaction with the azide, thioacetate, and dimethyl malonate anions and benzylamine gives the corresponding substituted products in an enantiomerically pure form with an inversion of the configuration in good yields. The methanolysis of (S)-5,6,7,8-tetrahydroquinolin-8-yl acetate in the presence of potassium carbonate and alkylation of the resulting thiol anion with alkyl halides in a one-pot reaction gives the 5,6,7,8-tetrahydroquinolin-8-yl thioether.
Key words
8-substituted quinolines - enzymatic acetylation - nucleophiles - stereospecific substitutions - asymmetric synthesis
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