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Synthesis of tempo containing chiral polymers for kinetic resolution of secondary alcohols.

Yücel, Ece Ayç
Optically pure secondary alcohols are important building blocks for the synthesis of chemicals used in pharmaceutical sciences. Kinetic resolution of secondary alcohols through selective oxidation of one enantiomer to the corresponding ketone is a classical and efficient method to obtain enantiopure alcohols. An oxidative kinetic resolution is achieved by exploiting two enantiomers’ unequal rates of oxidation reaction with a chiral reagent or catalyst. The general approach towards a kinetic resolution via alcohol oxidation utilizes nitroxyl radicals on a chiral environment. The oxidations with these radicals are highly efficient catalytic oxidations due to fast and efficient turnover and the use of inexpensive oxidants. In this study, 2,2,6,6-tetramethylpiperidine 1-oxyl (TEMPO) containing chiral polymers were synthesized via ring opening metathesis polymerization. Afterwards, the synthesized polymers were used as catalysts for the oxidative kinetic resolution of 1-phenyl ethanol. Morever, a TEMPO containing polymer was employed as a cathode material in the construction of a organic radical battery.