Azabicyclic amino acids by stereoselective dearomatizing cyclization of the enolates of N-nicotinoyl glycine derivatives

Gareth Arnott, Jonathan Clayden, Stuart D. Hamilton

    Research output: Contribution to journalArticlepeer-review

    Abstract

    On activation by pyridine N-acylation, enolates of N-nicotinoyl and N-isonicotinoyl glycine and alanine derivatives cyclize to yield 6,5-azabicyclic or 6,4-azaspirocyclic lactams. With an N-α-methyl-p-methoxybenzyl group the cyclization is diastereoselective; hydrogenation and deprotection yields azabicyclic amino acids in 94:6 er. © 2006 American Chemical Society.
    Original languageEnglish
    Pages (from-to)5325-5328
    Number of pages3
    JournalOrganic Letters
    Volume8
    Issue number23
    DOIs
    Publication statusPublished - 9 Nov 2006

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