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Synthesis of Benzomorphan Analogues by Intramolecular Buchwald–Hartwig Cyclization

✍ Scribed by Anton S. Khartulyari; Martin E. Maier

Publisher
John Wiley and Sons
Year
2007
Tongue
English
Weight
181 KB
Volume
2007
Category
Article
ISSN
1434-193X

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✦ Synopsis

Abstract

A new strategy toward the important class of benzomorphans is described. The key bond formation is based on an intramolecular Buchwald–Hartwig enolate arylation reaction. Thus, alkylation of piperidones with ortho‐bromobenzyl bromides provides the necessary substrates. In the presence of a palladium catalyst, a sterically hindered phosphane ligand, and a base, carbon–carbon bond formation to tricyclic benzomorphan derivatives takes place. After removal of the N‐protecting group, derivatization reactions are possible. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

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