Tetrahedron p. 1029 - 1040 (1998)
Update date:2022-08-04
Topics:
Cassayre, Jerome
Quiclet-Sire, Beatrice
Saunier, Jean-Baptiste
Zard, Samir Z.
N-Alkenyl trichloroacetamides, upon treatment with nickel powder and acetic acid in refluxing 2-propanol undergo reversible 4-exo radical cyclisation. The cyclised radical can be trapped in different ways leading to β-lactams. When the trap is omitted or not efficient enough, unusual irreversible 5-endo cyclisation occurs affording functionalised five-membered lactams. Synthesis of bicyclic γ-lactams has also been examined providing in few steps an access to the Sceletium alkaloids skeleton.
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