Indium- and zinc-mediated Barbier-type allylations of an N,N-(dimethylsulfamoyl)-protected aldimine and subsequent deprotection

Sara Källström, Tiina Saloranta, Adriaan J. Minnaard, Reko Leino

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    17 Citations (Scopus)

    Abstract

    Barbier-type Zn and In-mediated allylations of an N,N-(dimethylsulfamoyl)-protected aldimine with different allyl bromides were investigated for the preparation of N-homoallylic sulfamides. The desired N,N-(dimethylsulfamoyl)-protected products were obtained in moderate to high yields in THF as the optimal solvent. Their further derivatization was demonstrated by a facile preparation of a functionalized dehydropiperidine by an allylation/olefin metathesis reaction sequence. A high yielding deprotection of the N,N-dimethylsulfamoyl group was likewise demonstrated. (c) 2007 Elsevier Ltd. All rights reserved.
    Original languageUndefined/Unknown
    Pages (from-to)6958–6961
    Number of pages4
    JournalTetrahedron Letters
    Volume48
    Issue number39
    DOIs
    Publication statusPublished - 2007
    MoE publication typeA1 Journal article-refereed

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