643734-28-5Relevant articles and documents
A New Chemoselective Base-Mediated Protection/Deprotection Method for Aldehydes
Dixon, Darren J.,Scott, Mark S.,Luckhurst, Chris A.
, p. 2317 - 2320 (2007/10/03)
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.