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  • Title: Enantiomerically pure polyheterocyclic spiro-beta-lactams from trans-4-hydroxy-L-proline.
    Author: Cremonesi G, Dalla Croce P, Fontana F, La Rosa C.
    Journal: J Org Chem; 2010 Mar 19; 75(6):2010-7. PubMed ID: 20187611.
    Abstract:
    The "Staudinger ketene-imine reaction" between ketenes generated from natural O,N-protected trans-4-hydroxy-l-prolines and the N-benzyl-N-benzylideneamine led to mixtures of diastereoisomeric, enantiomerically pure pyrrolidine-derived spiro-beta-lactams with a relative cis configuration. These were transformed into the corresponding pyrroline-spiro-beta-lactams by means of treatment with a base and the new C=C double bond was submitted to a number of different reactions in order to evaluate its reactivity and obtain new polyheterocyclic enantiomerically pure spiro-beta-lactams.
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