The palladium-catalyzed aerobic kinetic resolution of secondary alcohols: reaction development, scope, and applications.

@article{Ebner2009ThePA,
  title={The palladium-catalyzed aerobic kinetic resolution of secondary alcohols: reaction development, scope, and applications.},
  author={David Christopher Ebner and Jeffrey Thomas Bagdanoff and Eric M Ferreira and Ryan M. L. McFadden and Daniel D Caspi and Raissa M. Trend and Brian M Stoltz},
  journal={Chemistry},
  year={2009},
  volume={15 47},
  pages={
          12978-92
        }
}
The first palladium-catalyzed enantioselective oxidation of secondary alcohols has been developed, utilizing the readily available diamine (-)-sparteine as a chiral ligand and molecular oxygen as the stoichiometric oxidant. Mechanistic insights regarding the role of the base and hydrogen-bond donors have resulted in several improvements to the original system. Namely, addition of cesium carbonate and tert-butyl alcohol greatly enhances reaction rates, promoting rapid resolutions. The use of… CONTINUE READING