Enantioselective Assembly of Tricyclic Tetrahydroquinoline Derivatives

Mustafa Zahrittin Kazancioğlu, Erbay Kalay, Elif Akın Kazancıoğlu, Vsevolod A. Peshkov

2019

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DOI 10.1002/slct.201902249
Data confidence 70 medium
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Abstract

Abstract A three‐step synthetic route towards enantioenriched tricyclic tetrahydroquinoline derivatives has been investigated. The first step involved the assembly of 4‐amino‐tetrahydroquinoline core through the asymmetric three‐component Povarov reaction of benzyl ( E )‐prop‐1‐en‐1‐ylcarbamate and p ‐anisidine with aliphatic aldehydes of various length bearing protected hydroxyl group. The alcohol was then deprotected and employed in an intramolecular reaction with a secondary amine of tetrahydroquinoline moiety producing desired tricyclic scaffolds.