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. ORCID: https://orcid.org/0000-0002-8442-7380 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 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.