Abstract
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.
| Original language | English |
|---|---|
| Pages (from-to) | 1029-1040 |
| Number of pages | 12 |
| Journal | Tetrahedron |
| Volume | 54 |
| Issue number | 7 |
| DOIs | |
| Publication status | Published - 12 Feb 1998 |
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