DNA-based hydrolytic kinetic resolution of epoxides

DNA-bound copper(II) complexes serve as catalysts for the hydrolytic kinetic resolution of 2-pyridyloxiranes in water. Selectivity factors of up to 2.7 were achieved, indicating a chirality transfer of DNA to epoxides via a coordinated metal ion.

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trans-2-[(2S,3S)-3-Phenyloxiranyl]pyridineC13H11NOEe = >95% ee[α]D20=-275 (c 3 × 10−3, EtOH)Source of chirality: preparative chiral HPLCAbsolute configuration: (2S,3S)