A New Chemoselective Base-Mediated Protection/Deprotection Method for Aldehydes

Darren J. Dixon, Mark S. Scott, Chris A. Luckhurst

    Research output: Contribution to journalArticlepeer-review


    A wide range of aldehydes was efficiently protected as pyrrole carbinol derivatives by direct addition of lithium pyrrolate in THF at -78°C. The protection is chemoselective towards aldehydes over ketones and the O-lithiated, O-protonated or O-silylated carbinols may be used to block the aldehyde from nucleophilic and basic reagents at low temperatures. Mild, basic deprotection using DBU, NaOMe or TBAF allows for in situ trapping-reactions (such as Wadsworth-Horner-Emmons olefination) of the released aldehyde.
    Original languageEnglish
    Pages (from-to)2317-2320
    Number of pages3
    Issue number15
    Publication statusPublished - 2003


    • Aldehydes
    • Chemoselective
    • Protecting-group
    • Pyrrole carbinol
    • Tandem reactions


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