1,5-stereocontrol in bismuth-mediated reactions between aldehydes and allyl bromides: Stereoselective synthesis of open-chain all-syn- and anti, anti-1,3,5-disposed trimethylalkanes

Norazah Bazar, Sam Donnelly, Hao Liu, Eric J. Thomas

    Research output: Contribution to journalArticlepeer-review

    Abstract

    The reaction of 5-benzyloxy-2,4-dimethylpent-2-enyl bromide with the bismuth species generated by reduction of bismuth(III) iodide by zinc powder gives an intermediate which reacts with aldehydes with useful levels of stereocontrol in favour of 1,5-anti-(3E)-5-methylalk-3-enols. Manipulation of protecting groups, stereoselective hydrogenation, and tosylate displacement using a higher-order cyanomethylcuprate leads to either all-syn or anti, anti-1,3,5-disposed trimethylalkanes. © Georg Thieme Verlag Stuttgart.
    Original languageEnglish
    Article numberD34809ST
    Pages (from-to)575-578
    Number of pages3
    JournalSYNLETT
    Issue number4
    DOIs
    Publication statusPublished - 2010

    Keywords

    • Aldehydes
    • Allylation
    • Diastereoselectivity
    • Hydrogenation
    • Organometallic reagents

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