Synlett

A new chemoselective base-mediated protection/deprotection method for aldehydes

DJ Dixon, MS Scott, CA Luckhurst

Index: Dixon, Darren J.; Scott, Mark S.; Luckhurst, Chris A. Synlett, 2003 , # 15 p. 2317 - 2320

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Citation Number: 18

Abstract

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 ...