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

Ferreira, Eric M. and Stoltz, Brian M. (2001) The Palladium-Catalyzed Oxidative Kinetic Resolution of Secondary Alcohols with Molecular Oxygen. Journal of the American Chemical Society, 123 (31). pp. 7725-7726. ISSN 0002-7863. https://resolver.caltech.edu/CaltechAUTHORS:20170215-134639074

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Abstract

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).


Item Type:Article
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http://dx.doi.org/10.1021/ja015791zDOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja015791zPublisherArticle
http://pubs.acs.org/doi/suppl/10.1021/ja015791zPublisherSupporting Information
ORCID:
AuthorORCID
Stoltz, Brian M.0000-0001-9837-1528
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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CaltechUNSPECIFIED
Camille and Henry Dreyfus FoundationUNSPECIFIED
Merck Research LaboratoriesUNSPECIFIED
Issue or Number:31
Record Number:CaltechAUTHORS:20170215-134639074
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20170215-134639074
Official Citation:The Palladium-Catalyzed Oxidative Kinetic Resolution of Secondary Alcohols with Molecular Oxygen Eric M. Ferreira and Brian M. Stoltz Journal of the American Chemical Society 2001 123 (31), 7725-7726 DOI: 10.1021/ja015791z
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:74330
Collection:CaltechAUTHORS
Deposited By: George Porter
Deposited On:15 Feb 2017 22:42
Last Modified:03 Oct 2019 16:37

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