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2005
Metathesis reactions
O 0286
Synthesis of Polycyclic Lactams and Sultams by a Cascade Ring-Closure Metatheand Subsequent Radical Cyclization. — Pyrrolines (IV), pre30- 047 sis/Isomerization
pared from N,N-bisallylamides (III) by ring-closure metathesis and subsequent isomerization promoted by ruthenium hydride complexes, undergo radical cyclization to provide polycyclic lactams like (VI). This overall sequence is applied to sulfonamides
(VIII) to furnish sultams (X). Combining the ring-closing metathesis, the izomerization
step and the radical cyclization results in a one-pot procedure and provides a short access to tri- or tetracyclic lactams, e.g. (VIa), and sultams, e.g. (Xb). — (BRESSY, C.;
MENANT, C.; PIVA*, O.; Synlett 2005, 4, 577-582; Lab. Chim. Org. Photochim.
Synth., CNRS, Univ. Claude Bernard Lyon, F-69622 Villeurbanne, Fr.; Eng.) —
H. Hoennerscheid
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