Rhodium(I)-Catalyzed Allenic Carbocyclization Reaction Affording δ- and ε-Lactams

This letter extends the scope of the rhodium(I)-catalyzed allenic Alder-ene carbocyclization reaction to the preparation of δ- and ε-lactams from amides. A variety of allenic propiolamides were cycloisomerized to give a number of unsaturated δ-lactams. In addition, allenic propargylamides give good...

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Veröffentlicht in:Organic letters 2007-01, Vol.9 (2), p.347-349
Hauptverfasser: Brummond, Kay M, Painter, Thomas O, Probst, Donald A, Mitasev, Branko
Format: Artikel
Sprache:eng
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Zusammenfassung:This letter extends the scope of the rhodium(I)-catalyzed allenic Alder-ene carbocyclization reaction to the preparation of δ- and ε-lactams from amides. A variety of allenic propiolamides were cycloisomerized to give a number of unsaturated δ-lactams. In addition, allenic propargylamides give good yields of the corresponding ε-lactams. Formation of lactams possessing these ring sizes has rarely been accomplished via transition-metal-catalyzed carbon−carbon bond forming strategies. Thus, this approach provides an alternative strategy for synthesizing these substructures.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol062842u