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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