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TitleTotal facial selectivity of a D-erythrosyl aromatic imine in [4π + 2π] cycloadditions; synthesis of 2-alkylpolyol 1,2,3,4-tetrahydroquinolines
Author(s)Ferreira, Juliana
Duarte, Vera C. M.
Noro, Jennifer Martins
Fortes, A. Gil
Alves, Maria José Chão
Issue date1-Feb-2016
PublisherRoyal Society of Chemistry
JournalOrganic and Biomolecular Chemistry
CitationFerreira, J., Duarte, V. C., Noro, J., Fortes, A. G., & Alves, M. J. (2016). Total facial selectivity of ad-erythrosyl aromatic imine in [4π+ 2π] cycloadditions; synthesis of 2-alkylpolyol 1, 2, 3, 4-tetrahydroquinolines. Organic & biomolecular chemistry, 14(10), 2930-2937
Abstract(s)Different electron-rich dienophiles were combined with the imine obtained from 2,4-O-benzylidene-D-erythrose and p-anisidine furnishing enantiomerically pure tetrahydroquinolines, by inverse electron-demand [4 pi + 2 pi] cycloaddition. The imine was also reacted with 2-substituted electron-rich 1,3-butadienes giving the diastereomeric pure product, resulting from the normal electron demand cycloaddition. The facial selectivity of both processes is proposed on the basis of a 1,4-relationship between the hydroxyl group and the nitrogen atom in the chiral N-(p-methoxyphenyl) imine derivative.
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Appears in Collections:CDQuim - Artigos (Papers)

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