1114455-26-3Relevant academic research and scientific papers
Addition of heteroatom nucleophiles to ketene dimers
Elledge, Beth,Harzmann, Gero D.,Ibrahim, Ahmad A.,Kerrigan, Nessan J.,Nalla, Divya,van Raaphorst, Max
, (2021/05/26)
An investigation of the reaction of heteroatom nucleophiles with ketene dimers, with an emphasis on a discussion of diastereoselectivity where applicable, is described. During this study we focused on the reaction of nitrogen-centred nucleophiles (Weinreb amine, lithiated Weinreb amide, and an amino acid derivative), and oxygen-centred nucleophiles (alkoxides). Simple Weinreb amide derivatives of ketene heterodimers were formed in moderate to excellent yield (up to 89%) and excellent retention of chirality (ee up to 91%), albeit with poor diastereoselectivity. The 2-pyridone-catalysed amine ring-opening was also applied to the asymmetric synthesis of a cinnabaramide A intermediate. Finally, the use of amide and alkoxide ring-opening nucleophiles enabled the development of a sequential one-pot reaction with benzaldehyde to afford δ-lactones in moderate yields (up to 47%) but with good diastereoselectivity (dr up to 24:1).
Synthesis of 1,3-diketones through ring-opening of ketoketene dimer β-lactones
Ibrahim, Ahmad A.,Smith, Stephen M.,Henson, Sarah,Kerrigan, Nessan J.
supporting information; experimental part, p. 6919 - 6922 (2010/05/18)
The reaction of ketoketene dimers with organolithium reagents afforded 1,3-diketones in good to excellent yields, and with good diastereoselectivity in some cases.
