Tetrahydro-β-carbolines, (S)-tetrahydroharman (8a) and (S)-1-phenyltetrahydro-β-carboline (8b), were asymmetrically synthesized starting from (R)-phenylglycinol and 1-benzyl-3-(2-bromoethyl)indole (1). Asymmetric synthesis of the 9-thio analogue (15) of 8a was also achieved.
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QAIS et al. (1991) studied this question.