Enantioselective hydrogenation of the imines 11−13, 27 and 30 with the Ru complex (R,R)-5 led to the tetrahydro-β-carbolines (1S)-14, (1R)-21 and (1S)-22, and the tetrahydroisoquinoline (1S)-31 with ee > 95%. By employing (S,S)-5 the enantiomers are accessible. The imines 11−12 and 27 were obtained by oxidation of racemic 14, 21 and 22 with KMnO4 in > 58% yield.
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Tietze et al. (2000) studied this question.
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