A novel synthesis of didehydroamino acid (DDAA) esters 5 is described, starting from aldimines 2. The mechanism for this reaction has been shown to involve the cycloaddition of an azomethine ylide 3 to an imine 2, followed by the base-catalysed ring-opening of the resulting imidazolidine intermediate 7. This novel method has also been extended to the synthesis of DDAA esters 5 catalysed by imines.
P. W. Groundwater, T. Sharif, A. Arany, D. E. Hibbs, M. B. Hursthouse, I. Garnett and M. Nyerges, J. Chem. Soc., Perkin Trans. 1, 1998, 2837 DOI: 10.1039/A803695K
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