Carbolithiation of S-alkenyl-N-aryl thiocarbamates: Carbanion arylation in a connective route to tertiary thiols

Daniele Castagnolo, Daniel J. Foley, Hatice Berber, Renzo Luisi, Jonathan Clayden

    Research output: Contribution to journalArticlepeer-review

    Abstract

    S-Alkenyl-N-arylthiocarbamates are formed from allylic alcohols by sigmatropic rearrangement and isomerization or C=C bond cleavage. They undergo carbolithiation with a range of organolithium reagents, generating benzyllithium intermediates in a stereospecific manner which may undergo N to C aryl migration to yield thiocarbamates with tertiary substituents. A simple base-promoted alcoholysis reveals a series of hindered tertiary thiols with branched carbon skeletons. © 2013 American Chemical Society.
    Original languageEnglish
    Pages (from-to)2116-2119
    Number of pages3
    JournalOrganic Letters
    Volume15
    Issue number9
    DOIs
    Publication statusPublished - 3 May 2013

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