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  • Title: Synthesis of functionally diverse and conformationally constrained polycyclic analogues of proline and prolinol.
    Author: Hanessian S, Papeo G, Angiolini M, Fettis K, Beretta M, Munro A.
    Journal: J Org Chem; 2003 Sep 19; 68(19):7204-18. PubMed ID: 12968869.
    Abstract:
    Alkylation of the monoenolate of N-Boc-l-pyroglutamic acid methyl ester with a variety of benzylic halides and their homologues gave the corresponding anti-C-4-alkylated products as major products. Formation of the N-Boc-iminium ion and Friedel-Crafts intramolecular cationic ring closure afforded a series of fused 1-azacyclodihydroindene derivatives with interesting topologies. Functional diversity was introduced via further manipulation of pendant groups on the original proline motif as well as on the aromatic moiety.
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