Synthesis of Optically Active Condensed Tetrahydropyridines from α-Amino Esters

Abstract

Optically active condensed dihydropyridones 6 could be synthesized from α-amino esters 2 or 3 and o-bromobenzyl bromides or heterocyclic analogues 1. These products resemble isoquinoline and β-carboline alkaloid structures and could be stereoselectively transformed into condensed 4-hydroxytetrahydropyridines 7 and 8 by reaction with Grignard reagents or reduction. Treatment of condensed 4-allyl or 4-homoallyl-4-hydroxypyridines 8 with N-iodosuccinimide undergoes halocyclization to bridged tricyclic tetrahydropyridines 9 and 10.

Key words

amino acids - carbolines - isoquinolines - asymmetric synthesis - heterocycles

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Full details have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC 606388. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK.