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.
Barrett
A G
AG
Department of Chemistry, Imperial College of Science, Technology and Medicine, London SW7 2AY, United Kingdom. agmb@ic.ac.uk
Roberts
R S
RS
Schröder
J
J
D002845:Chromatography / Q000379:methods; D020650:Combinatorial Chemistry Techniques / Q000379:methods*; D003998:Dicarboxylic Acids / Q000737:chemistry; D009636:Norbornanes / Q000737:chemistry; D009942:Organometallic Compounds / Q000737:chemistry; D004364:Pharmaceutical Preparations / Q000138:chemical synthesis / Q000302:isolation & purification; D010720:Phosphines / Q000737:chemistry; D012428:Ruthenium / Q000737:chemistry
D003998:Dicarboxylic Acids; D009636:Norbornanes; D009942:Organometallic Compounds; D004364:Pharmaceutical Preparations; D010720:Phosphines; D012428:Ruthenium