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Synthesis of Alkaloids of Galipea officinalis by Alkylation of an α‐Amino Nitrile
Author(s) -
Shahane Saurabh,
Louafi Fadila,
Moreau Julie,
Hurvois JeanPierre,
Renaud JeanLuc,
van de Weghe Pierre,
Roisnel Thierry
Publication year - 2008
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200800512
Subject(s) - chemistry , hydrogenolysis , nitrile , alkylation , nitrogen atom , diastereomer , catalysis , alkyl , organic chemistry , enantioselective synthesis , medicinal chemistry , stereochemistry
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 NaBH 4 ‐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)