A convenient synthesis of phosphonomethyl α, β-unsaturated γ-lactams. Issue 40 (30th September 2015)

• Record Type: Journal Article
• Authors: Abdelli, Abderrahmen; Efrit, Mohamed Lotfi; Gaucher, Anne; M'rabet, Hedi; Prim, Damien
• Is Part Of: Tetrahedron letters. Volume 56:Issue 40(2015)
• Page Start: 5397
• Page End: 5400
• Publication Date: 2015-09-30
• Subjects: Keto-esters -- γ-Lactams -- Allylphosphonates -- Michael addition -- Nef reaction; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2015.07.088
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Abstract: 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.