Stereoselective synthesis of cyclobutyl GABA analogues and related compounds from (-)-(S)-verbenone

Albertina G. Moglioni, Beatriz N. Brousse, Angel Álvarez-Larena, Graciela Y. Moltrasio, Rosa M. Ortuo

    Research output: Contribution to journalArticleResearchpeer-review

    40 Citations (Scopus)

    Abstract

    The highly stereoselective conjugate addition of nitromethane to α,β-unsaturated cyclobutyl esters derived from (-)-(S)-verbenone has been executed to afford the adducts as single stereoisomers in good yields. These products furnish cyclobutyl GABA analogues and γ-lactams which, in turn, can be used as precursors of pyrrolidines. Moreover, both the enantiopure γ-nitro esters and the derived γ-amino esters are potentially useful for incorporation into γ-amino peptidomimetics. © 2002 Elsevier Science Ltd. All rights reserved.
    Original languageEnglish
    Pages (from-to)451-454
    JournalTetrahedron Asymmetry
    Volume13
    Issue number5
    DOIs
    Publication statusPublished - 5 Apr 2002

    Fingerprint Dive into the research topics of 'Stereoselective synthesis of cyclobutyl GABA analogues and related compounds from (-)-(S)-verbenone'. Together they form a unique fingerprint.

    Cite this