Synthesis of aminocyclobutanes through ring expansion of N-vinyl-beta-lactams.
Both eight-membered enamide rings and fused [4.2.0]aminocyclobutane-containing delta-lactams can be accessed from N-vinyl-beta-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 delta-lactams in a diastereoselective manner.
Cheung
Lawrence L W
LL
Department of Chemistry, University of Toronto, 80 St. George Street, Toronto M5S 3H6, Canada.
Yudin
Andrei K
AK
D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D003503:Cyclobutanes / Q000138:chemical synthesis* / Q000737:chemistry; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D047090:beta-Lactams / Q000138:chemical synthesis* / Q000737:chemistry
D003503:Cyclobutanes; D006571:Heterocyclic Compounds; D047090:beta-Lactams