Synthesis of Optically Active Condensed Tetrahydropyridin-3-ones as Precursors of Alkaloid Analogues

Heike Faltz; Alexander Radspieler; Jürgen Liebscher

doi:10.1055/s-1997-1521

Synlett 1997; 1997(9): 1071-1072
DOI: 10.1055/s-1997-1521

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Synthesis of Optically Active Condensed Tetrahydropyridin-3-ones as Precursors of Alkaloid Analogues

Heike Faltz, Alexander Radspieler, Jürgen Liebscher^*

^*Institut für Chemie, Humboldt-Universität Berlin, Hessische Str. 1-2, D-10115 Berlin, Germany, Fax: 49-30-2093 7343, e-mail: liebscher@chemie.hu-berlin.de

Abstract

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Reaction of α-aminoester with o-bromobenzylbromide or 3-bromo-2-bromomethylindole 1 gives N-alkylation products 3, which further undergo intramolecular acylation upon Br/Li-exchange. This sequence represents the first access to optically active condensed tetrahydropyridin-3-ones 4.

tetrahydroisoquinolin-4-ones - tetrahydroindolopyridin-4-ones - amino acid derivatives - halogen-metal-exchange - optical activity

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