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Dynamic Kinetic Resolution using a Palladium / QuinoxP* Complex
Ji et al. have reported a facile enantioselective organic synthesis via dynamic kinetic resolution (DKR) using a reactive Pd catalyst(1) prepared from palladium(II) acetate and (R, R)-QuinoxP*. According to their report, by the use of a catalyst 1, and a racemic starting material 2, the C-N coupling reaction prefers to proceed with the enantiomer 2 having a higher reaction rate, and the desired coupling product is given with high ee. Using this reaction, another enantiomer having a lower reaction rate is epimerized and shifted to form the higher reaction enantiomer by DKR. As a result, a partial structure of hepatitis C virus inhibitor “ruzaswir” is successfully synthesized. In this way, the catalyst 1 is effective for obtaining highly enantio-controlled compounds from racemic compounds thereby attracting attention as a way to synthesize optically active compounds.1-3)
References
- 1) A Rational Pre-catalyst Design for Bis-Phosphine Mono-oxide Palladium Catalyzed Reactions
- 2) Enantioselective Synthesis of Hemiaminals via Pd-Catalyzed C−N Coupling with Chiral Bisphosphine Mono-oxides
- 3) Searching for Practically Useful P-Chirogenic Phosphine Ligands