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1,3-Dipolar cycloadditions to unsymmetrical ketone-derived chiral stabilized azomethine ylides: strategies for the synthesis of highly substituted amino acids

Aldous, D.J., Drew, M.G.B., Draffin, W.N., Hamelin, E.M.N., Harwood, L.M. and Thurairatnam, S. (2005) 1,3-Dipolar cycloadditions to unsymmetrical ketone-derived chiral stabilized azomethine ylides: strategies for the synthesis of highly substituted amino acids. Synthesis-Stuttgart (19). pp. 3271-3278. ISSN 0039-7881

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To link to this item DOI: 10.1055/s-2005-918487

Abstract/Summary

We report herein, the first generation of unsymmetrical ketone-derived chiral stabilized azomethine ylides. Intrairiolecular and intermolecular cycloaddition strategies have been utilized to synthesize both an enantiornerically pure bicyclic proline derivative and an enantionierically pure beta-hydroxy-alpha-amino acid.

Item Type:Article
Refereed:Yes
Divisions:Faculty of Life Sciences > School of Chemistry, Food and Pharmacy > Department of Chemistry
ID Code:10956
Uncontrolled Keywords:azomethine ylide, beta-hydroxy-alpha-amino acid, proline, intramolecular, cycloaddition, ENANTIOCONTROLLED CONSTRUCTION, STEREOSELECTIVE-SYNTHESIS, PROLINE, DERIVATIVES, 5,5-DIMETHYLPROLINE, GENERATION, CONFORMATION

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