PROTECTING GROUPS THAT INCORPORATE A 4-PENTENYL ACETAL MOIETY CAN BE CLEAVED UNDER NEUTRAL CONDITIONS

Article abstract of DOI:10.1016/S0040-4039(00)82394-1

Alcohols can be protected as their 4-pentenyloxymethyl (POM) ethers, and regenerated therefrom by treatment with NBS in CH3CN/H2O.Ketones and aldehydes are converted into ketals by reaction with 5-hexen-1,2-diol.Regeneration occurs by treatment with NBS or Hg(OAc)2 in aqueous media.Vicinal diols are are converted into acetals by reaction with 4-pentenal.Deprotection is achieved by sequential oxidative and reductive steps.