Abstract magnified image New tetrahydroisoquinolines were synthesized by the Pictet‐Spengler reaction. Influence of a wide range of aryl and heteroaryl aldehydes, was investigated in the cyclization step with 3,4‐dimethoxyphenylethylamine 1 , L‐DOPA 2 and L‐3,4‐dimethoxyphenylalanine methyl ester 3 . Compounds 2 and 3 served as probes to assess the efficiency of two Pictet‐Spengler reactions with respect to their diastereoselectivity, in order to obtain optically active diastereoisomers. Cis ‐ and trans ‐diastereoisomers were obtained in short reaction times with moderate to good isolated yields (20‐79%). Both nmr and X‐ray analyses confirmed the expected diastereoisomer configurations.
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Aubry et al. (2006) studied this question.
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