An Imine-Based Route to Polycyclic Chlorinated ε-Lactams by Formation of C–C Bonds as Key Steps

Fabian Brockmeyer; Timo Stalling; Jürgen Martens

doi:10.1055/s-0032-1316751

Synthesis, Table of Contents

Synthesis 2012; 44(18): 2947-2958
DOI: 10.1055/s-0032-1316751

paper

An Imine-Based Route to Polycyclic Chlorinated ε-Lactams by Formation of C–C Bonds as Key Steps

Fabian Brockmeyer

Institut für Reine und Angewandte Chemie, Carl von Ossietzky Universität Oldenburg, P. O. Box 2503, 26111 Oldenburg, Germany, Email: juergen.martens@uni-oldenburg.de

,

Timo Stalling

Institut für Reine und Angewandte Chemie, Carl von Ossietzky Universität Oldenburg, P. O. Box 2503, 26111 Oldenburg, Germany, Email: juergen.martens@uni-oldenburg.de

,

Jürgen Martens*

Institut für Reine und Angewandte Chemie, Carl von Ossietzky Universität Oldenburg, P. O. Box 2503, 26111 Oldenburg, Germany, Email: juergen.martens@uni-oldenburg.de

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Abstract

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Abstract

A two-step sequence for the conversion of heterocyclic imines to saturated and unsaturated polycyclic chlorinated ε-lactams is disclosed. In the first step, an acyl chloride addition followed by a substitution is used to achieve unsaturated methoxyamides. The final lactamization to two different classes of polycyclic ε-lactams via formation of a C–C bond is realized by the use of metal chlorides as Lewis acid and as a source of chloride. The potential of the ε-lactams in subsequent reactions is demonstrated by an elimination reaction.

Key words

heterocycles - imines - lactams - ring closure - ring contraction - Schiff bases

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