Issue 10, 1988

X[double bond, length half m-dash]Y–ZH systems as potential 1,3-dipoles. Part 11. Stereochemistry of 1,3-dipoles generated by the decarboxylative route to azomethine ylides

Abstract

The decarboxylative reaction of aryl aldehydes with cyclic secondary α-amino acids or primary α-amino acids in the presence of N-methyl- or N-phenyl-maleimide leads, via an intermediate azomethine ylide, to mixtures of bicyclic pyrrolidine cycloadducts in good yield. Cyclic secondary α-amino acids, where the carboxylic group is non-benzylic, give cycloadducts arising from a stereospecifically generated anti-dipole. Acyclic α-amino acids, and cyclic secondary α-amino acids with the carboxylic group located at a benzylic site, give rise to cycloadducts derived from both anti- and syn-configurations of the intermediate azomethine glides. The reactions show little discrimination between endo- and exo-transition states for the cycloadditions.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1988, 2693-2701

X[double bond, length half m-dash]Y–ZH systems as potential 1,3-dipoles. Part 11. Stereochemistry of 1,3-dipoles generated by the decarboxylative route to azomethine ylides

R. Grigg, S. Surendrakumar, S. Thianpatanagul and D. Vipond, J. Chem. Soc., Perkin Trans. 1, 1988, 2693 DOI: 10.1039/P19880002693

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