Total facial selectivity of a D-erythrosyl aromatic imine in [4π + 2π] cycloadditions; synthesis of 2-alkylpolyol 1,2,3,4-tetrahydroquinolines

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 [4π + 2π] cycloaddition. The imine was also reacted with 2-substituted electron-rich 1,3-buta...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2016-01, Vol.14 (10), p.2930-2937
Main Authors: Ferreira, Juliana, Duarte, Vera C M, Noro, Jennifer, Gil Fortes, António, Alves, Maria J
Format: Article
Language:English
Subjects:
Cycloaddition Reaction
Imines - chemistry
Models, Molecular
Quinolines - chemistry
Spectrometry, Mass, Electrospray Ionization
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Summary: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 [4π + 2π] 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.
ISSN:1477-0520
1477-0539
DOI:10.1039/c5ob02594j