A convenient synthesis of phosphonomethyl α,β-unsaturated γ-lactams

[Display omitted] A versatile access to diversely substituted α,β-unsaturated γ-lactams is described using a common allylphosphonate precursor. The construction of the γ-lactam motive is based on two steps including a key sequential one-pot Michael addition–Nef sequence that allows the preparation o...

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Bibliographic Details
Published in:Tetrahedron letters 2015-09, Vol.56 (40), p.5397-5400
Main Authors: Abdelli, Abderrahmen, Efrit, Mohamed Lotfi, Gaucher, Anne, M’rabet, Hedi, Prim, Damien
Format: Article
Language:English
Subjects:
Allylphosphonates
Keto-esters
Michael addition
Nef reaction
γ-Lactams
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Summary:[Display omitted] A versatile access to diversely substituted α,β-unsaturated γ-lactams is described using a common allylphosphonate precursor. The construction of the γ-lactam motive is based on two steps including a key sequential one-pot Michael addition–Nef sequence that allows the preparation of keto-ester intermediates. Our methodology allowed the selective installation of various alkyl, cycloalkyl and aryl substituents as well as a valuable phosphonomethyl fragment at positions 1 and 3 of the heterocycle.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2015.07.088