A novel synthesis of didehydroamino acid esters from azomethine ylides

PW Groundwater, T Sharif, A Arany, DE Hibbs…

Index: Groundwater, Paul W.; Sharif, Toqir; Arany, Andrea; Hibbs, David E.; Hursthouse, Michael B.; Garnett, Ian; Nyerges, Miklos Journal of the Chemical Society - Perkin Transactions 1, 1998 , # 17 p. 2837 - 2846

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Citation Number: 20

Abstract

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.