Synlett · 1998 · 42 citations · 0 references
Natural SciencesChemistryCatalysisOrganic ChemistryReaction EngineeringOxidation ReactionsOxidation-reduction ReactionsOxidation-reduction ConditionsSelective DeprotectionSelective OxidationSilyl Ether DeprotectionSilyl Ether ProtectionSilyl Protecting Groups
The selective oxidation/deprotection of allylic and benzylic silyl ethers to give aldehydes can be achieved by hydride abstraction with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) under neutral conditions. This reaction is possible in the presence of a variety of silyl protecting groups, as in 2 → 3, and even PMB ethers and PMP acetals, as in 14 → 15, which are normally labile under DDQ oxidation conditions.