Synthesis of (-)-(S, S)-clemastine by invertive N → C aryl migration in a lithiated carbamate

Anne M. Fournier, Robert A. Brown, William Farnaby, Hideki Miyatake-Ondozabal, Jonathan Clayden

    Research output: Contribution to journalArticlepeer-review

    Abstract

    The first enantioselective synthesis of the antihistamine agent clemastine, as its (S,S)-stereoisomer, has been achieved by ether formation between a proline-derived chloroethylpyrrolidine and an enantiomerically enriched tertiary alcohol. The tertiary alcohol was formed from the carbamate derivative of α-methyl-p-chlorobenzyl alcohol by invertive aryl migration on lithiation. The (S,S)-stereochemistry of the product confirms the invertive nature of the rearrangement. © 2010 American Chemical Society.
    Original languageEnglish
    Pages (from-to)2222-2225
    Number of pages3
    JournalOrganic Letters
    Volume12
    Issue number10
    DOIs
    Publication statusPublished - 21 May 2010

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