Impurity Annihilation:  Chromatography-Free Parallel Mitsunobu Reactions

Mitsunobu reaction of an alcohol ROH with a carboxylic acid, phthalimide, or N-hydroxyphthalimide (NuH) using DNAD (4) and (diphenylphosphino)polystyrene (11) gave the products RNu. Ring-opening metathetic polymerization of the side product DNADH(2) (3) using Cl(2)(Cy(3)P)(2)Ru=CHPh (13) and filtration, to remove poly(DNADH(2)), (diphenylphosphino)polystyrene 11, its oxide, and its adduct with excess DNAD, gave RNu (43-100%, 86-96% purity) without recourse to chromatography.