Synlett 2005(4): 577-582  
DOI: 10.1055/s-2005-862386
LETTER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Polycyclic Lactams and Sultams by a Cascade Ring-Closure Metathesis/Isomerization and Subsequent Radical Cyclization

Cyril Bressy, Christine Menant, Olivier Piva*
Université Claude Bernard LYON I, UMR 5181 CNRS, Laboratoire de Chimie Organique-Photochimie et Synthèse, Bat Raulin, 43, Bd du 11 Novembre 1918, 69622 Villeurbanne Cedex, France
Fax: +33(4)72448136; e-Mail: piva@univ-lyon1.fr;
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Publikationsverlauf

Received 24 November 2004
Publikationsdatum:
22. Februar 2005 (online)

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Abstract

Starting from readily available substrates, a new one-pot procedure has been devised to prepare polycyclic lactams and sultams. 2-Pyrrolines obtained from N,N-bisallylamides by ring-closure metathesis and subsequent isomerization promoted by ruthenium hydride complexes can undergo radical cyclization to furnish polycyclic lactams in good yields. The process was successfully conducted on bisallylsulfonamides to give the corresponding sultams.