1346004-29-2Relevant academic research and scientific papers
Simple Aza -conjugate addition methodology for the synthesis of isoindole nitrones and 3,4-dihydroisoquinoline nitrones
Peacock, Lucy R.,Chapman, Robert S. L.,Sedgwick, Adam C.,Bull, Steven D.,Mahon, Mary F.,Amans, Dominique
, p. 994 - 997 (2015/03/18)
Aryl-aldehydes containing ortho-substituted α,β-unsaturated carboxylic acid derivatives react with hydroxylamine to afford reactive N-hydroxy-carbinolamine intermediates that undergo intramolecular aza-conjugate addition reactions to afford isoindole nitrones and 3,4-dihydroisoquinoline nitrones in good yield. Conditions have been developed to reduce these isoindole nitrones to their corresponding hydroxylamine, enamine, and amine derivatives. Isoindole nitrones react with dimethyl acetylenedicarboxylate (DMAD) via a [4 + 2]-cycloaddition/deamination pathway to afford substituted naphthalene derivatives, while 3,4-dihydroisoquinoline nitrones react with DMAD via a [1,3]-dipolar cycloaddition pathway to afford tricyclic heteroarenes.
Intramolecular ester enolate-imine cyclization reactions for the asymmetric synthesis of polycyclic β-lactams and cyclic β-amino acid derivatives
Evans, Caroline D.,Mahon, Mary F.,Andrews, Philip C.,Muir, James,Bull, Steven D.
, p. 6276 - 6279 (2012/02/01)
Enolates of chiral N-(α-methyl-p-methoxybenzyl)-ω-imino-esters undergo intramolecular cyclization reactions to afford (syn)-aza-anions of β-amino esters in high dr that cyclize to afford N-(α-methyl-p- methoxybenzyl)-β-lactams that can be readily deprotec
