203245-07-2Relevant academic research and scientific papers
β- and γ-lactams by nickel powder mediated 4-exo or 5-endo radical cyclisations. A concise construction of the mesembrine skeleton
Cassayre, Jerome,Quiclet-Sire, Beatrice,Saunier, Jean-Baptiste,Zard, Samir Z.
, p. 1029 - 1040 (2007/10/03)
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.
