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Published August 8, 2001 | Supplemental Material
Journal Article Open

The Palladium-Catalyzed Oxidative Kinetic Resolution of Secondary Alcohols with Molecular Oxygen


The oxidation of secondary alcohols is one of the most common and well-studied reactions in chemistry. Although excellent catalytic enantioselective methods exist for a variety of oxidation processes, such as epoxidation, dihydroxylation, and aziridination, it is surprising that there are relatively few catalytic enantioselective examples of the ubiquitous alcohol oxidation. In connection with a general program dealing with the discovery of new catalytic oxidation systems, we present herein the development of a catalytic oxidative kinetic resolution of secondary alcohols that uses molecular oxygen as the terminal oxidant (see Scheme 1).

Additional Information

© 2001 American Chemical Society. Received March 9, 2001. Revised Manuscript Received June 19, 2001. We are grateful to the California Institute of Technology, the Camille and Henry Dreyfus Foundation, and the Merck Research Laboratories for generous financial support. B.M.S. thanks the Camille and Henry Dreyfus Foundation for a New Faculty Award. We thank the MacMillan group for generously sharing their HPLC and GC equipment. We acknowledge Professors John E. Bercaw, Robert H. Grubbs, and David W. C. MacMillan and their groups for chemicals and helpful discussions.

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