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  • Title: Highly efficient solid-phase oxidative cleavage of olefins by OsO4-NalO4 in the intramolecular N-acyliminium Pictet-Spengler reaction.
    Author: Nielsen TE, Meldal M.
    Journal: Org Lett; 2005 Jun 23; 7(13):2695-8. PubMed ID: 15957924.
    Abstract:
    [reaction: see text] In the present investigation, solid-supported peptide olefins were converted quantitatively to aldehydes via the OsO(4)-NaIO(4)-mediated oxidative cleavage reaction. Addition of DABCO was essential to efficiently suppress the formation of hydroxymethyl ketone side products. The generated aldehydes were used in intramolecular N-acyliminium Pictet-Spengler reactions to produce highly pure pyrroloisoquinoline derivatives. The methodology was extended to allylglycine derivatives to enable the incorporation of pyrroloisoquinoline scaffolds within peptides.
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