Issue 10, 1988
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

X[double bond, length half m-dash]Y–ZH systems as potential 1,3-dipoles. Part 12. Mechanism of formation of azomethine ylides via the decarboxylative route from α-amino acids

Ronald Grigg,   Jonathan Idle,   Peter McMeekin,   Sivagnanasundram Surendrakumar  and  David Vipond  

Abstract

The effect of temperature, solvent, and type of aldehyde on the stereospecific or stereoselective formation of azomethine ylides by the decarboxylative condensation of aldehydes with three types of α-amino acids, (i) cyclic secondary α-amino acids, (ii) cyclic secondary α-amino acids with a benzylic carboxy group, and (iii) acyclic primary α-amino acids, has been studied. Stereospecific anti-dipole formation in (i) and temperature dependent stereoselective anti-dipole formation in (ii) and (iii) is inferred from the stereochemistry of cycloadducts of the azomethine ylides with N-methylmaleimide. These results are used to support a mechanistic scheme involving loss of carbon dioxide from intermediate oxazolidin-5-ones in a stereospecific cycloreversion reaction.

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Article information

DOI
https://doi.org/10.1039/P19880002703
Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1988, 2703-2713

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X[double bond, length half m-dash]Y–ZH systems as potential 1,3-dipoles. Part 12. Mechanism of formation of azomethine ylides via the decarboxylative route from α-amino acids

R. Grigg, J. Idle, P. McMeekin, S. Surendrakumar and D. Vipond, J. Chem. Soc., Perkin Trans. 1, 1988, 2703 DOI: 10.1039/P19880002703

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