Synthesis of α2,23-diamino acids by double stereodifferentiation aldol addition of oxazolidinone enolates to N-(tert-butylsulfinyl) imines

Andrea Guerrini, Greta Varchi, Cristian Samorì, Arturo Battaglia

    Research output: Contribution to journalArticlepeer-review

    9 Scopus citations

    Abstract

    A novel application of Seebach's "SRS" synthetic principle works efficiently when conformationally restrained trisubstituted chiral α2,23-diamino acids are synthesized by double stereoinduction reactions of chiral oxazolidinone enolates with N-sulfinyl aldimines. Two stereoisomers were isolated in a form of 1′-(sulfinylamino) oxazolidinones and bicyclic 1H,3H-imidazo[1,5-c]oxazole-1,5(6H)-diones, from which the α2,23-diamino acids are obtained by selective deprotection methodologies. Among a variety of highly functionalized diamino acids, this highly diastereoselective protocol provides a synthetic route for yet unreported C-glycosyl and α-nucleoside diamino acids.

    Original languageEnglish (US)
    Pages (from-to)3834-3844
    Number of pages11
    JournalEuropean Journal of Organic Chemistry
    Issue number22
    DOIs
    StatePublished - Aug 2008

    Keywords

    • Amino acids
    • Antifungal agents
    • Diastereoselectivity
    • Nitrogen heterocycles
    • Oxygen heterocycles
    • Peptidomimetics

    ASJC Scopus subject areas

    • Physical and Theoretical Chemistry
    • Organic Chemistry

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