A New Chemoselective Base-Mediated Protection/Deprotection Method for Aldehydes
- 7 November 2003
- journal article
- letter
- Published by Georg Thieme Verlag KG in Synlett
- Vol. 2003 (15) , 2317-2320
- https://doi.org/10.1055/s-2003-42470
Abstract
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.Keywords
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