Synthesis of Bicyclic Lactams via Ring Closing Olefin Metathesis and Intramolecular Heck Reaction

Michael Lennartz; Eberhard Steckhan

doi:10.1055/s-2000-6527

Synlett 2000; 2000(3): 319-322
DOI: 10.1055/s-2000-6527

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Synthesis of Bicyclic Lactams via Ring Closing Olefin Metathesis and Intramolecular Heck Reaction

Michael Lennartz^* , Eberhard Steckhan

^*Kekulé-Institut für Organische Chemie und Biochemie der Universität Bonn, Gerhard-Domagk-Str. 1, D-53121 Bonn, Germany; Fax +49 2 28 73 56 83; E-mail: steckhan@uni-bonn.de

Abstract

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The application of the ring closing olefin metathesis and the intramolecular Heck reaction as key steps in the synthesis of 6,5- and 7,5-fused enantiomerically pure bicyclic lactams starting from a chiral pyrrolidone is shown. The diolefinic cyclization precursors can be obtained by a combined electrochemical oxidation-N-acyliminium coupling reaction and a subsequent N-alkylation using an unsaturated alkyl bromide.

cyclizations - lactams - metathesis - Heck reaction - electrooxidation

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