XY–ZH systems as potential 1,3-dipoles. Part 12. Mechanism of formation of azomethine ylides via the decarboxylative route from α-amino acids
- 1 January 1988
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 10,p. 2703-2713
- https://doi.org/10.1039/p19880002703
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.Keywords
This publication has 5 references indexed in Scilit:
- X=Y-ZH Systems as potential 1,3-dipolesTetrahedron, 1988
- XY–ZH systems as potential 1,3-dipoles. Part 10. The decarboxylative route to azomethine ylides. Background and relevance to pyridoxal decarboxylasesJournal of the Chemical Society, Perkin Transactions 1, 1988
- XY–ZH Systems as potential 1,3-dipoles. Part 8. Pyrrolidines and Δ5-pyrrolines (3,7-diazabicyclo[3.3.0]octenes) from the reaction of imines of α-amino acids and their esters with cyclic dipolarophiles. Mechanism of racemisation of α-amino acids and their esters in the presence of aldehydesJournal of the Chemical Society, Perkin Transactions 1, 1986
- XY–ZH systems as potential 1,3-dipoles. Part 1. Background and scopeJournal of the Chemical Society, Perkin Transactions 1, 1984
- Alkylation of amino acids without loss of the optical activity: preparation of .alpha.-substituted proline derivatives. A case of self-reproduction of chiralityJournal of the American Chemical Society, 1983