Synthesis of Aminocyclobutanes through Ring Expansion of N-Vinyl-β-Lactams

Synthesis of Aminocyclobutanes through Ring Expansion of N-Vinyl-β-Lactams

Both eight-membered enamide rings and fused [4.2.0]aminocyclobutane-containing δ-lactams can be accessed from N-vinyl-β-lactams. The eight-membered rings are made through a [3,3] sigmatropic rearrangement. At elevated temperature, the eight-membered lactam undergoes electrocyclization to furnish fus...

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Veröffentlicht in:Organic letters 2009-03, Vol.11 (6), p.1281-1284
Hauptverfasser: Cheung, Lawrence L. W, Yudin, Andrei K
Format: Artikel
Sprache:eng
Schlagworte:
beta-Lactams - chemical synthesis
beta-Lactams - chemistry
Catalysis
Combinatorial Chemistry Techniques
Cyclization
Cyclobutanes - chemical synthesis
Cyclobutanes - chemistry
Heterocyclic Compounds - chemical synthesis
Heterocyclic Compounds - chemistry
Molecular Structure
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Zusammenfassung:Both eight-membered enamide rings and fused [4.2.0]aminocyclobutane-containing δ-lactams can be accessed from N-vinyl-β-lactams. The eight-membered rings are made through a [3,3] sigmatropic rearrangement. At elevated temperature, the eight-membered lactam undergoes electrocyclization to furnish fused cyclobutane δ-lactams in a diastereoselective manner.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol900118d