S. Shahane, F. Louafi, J. Moreau
Sep 1, 2008
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Journal
European Journal of Organic Chemistry
Abstract
A new synthetic approach directed towards the synthesis of naturally occurring 2-alkyl-tetrahydroquinolines is described. The C–C bonds in the α position relative to the nitrogen atom were formed by the reversal of the polarity of the C=N bond of α-amino nitrile 6, which was prepared electrochemically from 1-(phenylethyl)-tetrahydroquinoline. A NaBH4-mediated reductive decyanation process furnished benzylic amines 16a–d as mixtures of diastereomers (50–60 % de). The catalytic hydrogenolysis of these amines was performed in the presence of Pearlman's catalyst to give the tetrahydroquinolines 17a–d in yields ranging from 70 % to 95 %. Methylation of the free nitrogen atom afforded the title compounds 1–4 in 70–90 % yields.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)