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Catalytic Enantioselective Carbon–Oxygen Bond Formation: Phosphine-Catalyzed Synthesis of Benzylic Ethers via the Oxidation of Benzylic C–H Bonds

Ziegler, Daniel T. and Fu, Gregory C. (2016) Catalytic Enantioselective Carbon–Oxygen Bond Formation: Phosphine-Catalyzed Synthesis of Benzylic Ethers via the Oxidation of Benzylic C–H Bonds. Journal of the American Chemical Society, 138 (37). pp. 12069-12072. ISSN 0002-7863. http://resolver.caltech.edu/CaltechAUTHORS:20160919-131412998

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Abstract

Benzylic alcohols and ethers are common subunits in bioactive molecules, as well as useful intermediates in organic chemistry. In this Communication, we describe a new approach to the enantioselective synthesis of benzylic ethers through the chiral phosphine-catalyzed coupling of two readily available partners, γ-aryl-substituted alkynoates and alcohols, under mild conditions. In this process, the alkynoate partner undergoes an internal redox reaction. Specifically, the benzylic position is oxidized with good enantioselectivity, and the alkyne is reduced to the alkene.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/jacs.6b08486DOIArticle
http://pubs.acs.org/doi/abs/10.1021/jacs.6b08486PublisherArticle
http://pubs.acs.org/doi/suppl/10.1021/jacs.6b08486PublisherSupporting Information
ORCID:
AuthorORCID
Fu, Gregory C.0000-0002-0927-680X
Additional Information:© 2016 American Chemical Society. Received: August 13, 2016; Publication Date (Web): September 12, 2016. Support has been provided by the National Institutes of Health (National Institute of General Medical Sciences, R01-GM57034 and R01-GM062871). We thank William Reichard, Jun Myun Ahn (X-ray crystallography), and Dr. Michael K. Takase (X-ray crystallography) for assistance. The authors declare no competing financial interest.
Funders:
Funding AgencyGrant Number
NIHR01-GM57034
NIHR01-GM062871
Record Number:CaltechAUTHORS:20160919-131412998
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20160919-131412998
Official Citation:Catalytic Enantioselective Carbon–Oxygen Bond Formation: Phosphine-Catalyzed Synthesis of Benzylic Ethers via the Oxidation of Benzylic C–H Bonds Daniel T. Ziegler and Gregory C. Fu Journal of the American Chemical Society 2016 138 (37), 12069-12072 DOI: 10.1021/jacs.6b08486
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:70432
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:28 Sep 2016 18:51
Last Modified:12 Dec 2016 21:53

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