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Synthesis of Optically Active Constrained 2-Substituted Norstatines:  A Straightforward Application of Seebach's “SRS” Synthetic Principle

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journal contribution
posted on 24.12.2004, 00:00 by Arturo Battaglia, Andrea Guerrini, Carlo Bertucci
A straightforward two-step methodology of synthesis of optically active (2R)-substituted norstatines via addition of N-tert-butoxycarbonyl-substituted aldimines to (2S)-chiral enolates of 1,3-dioxolan-4-ones has been developed. In particular, the use of the natural (2S)-malic acid is examined for the synthesis of potential GABAergic spirocyclic γ-lactams.