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Catalytic Asymmetric Reductive Acyl Cross-Coupling: Synthesis of Enantioenriched Acyclic α,α-Disubstituted Ketones

Cherney, Alan H. and Kadunce, Nathaniel T. and Reisman, Sarah E. (2013) Catalytic Asymmetric Reductive Acyl Cross-Coupling: Synthesis of Enantioenriched Acyclic α,α-Disubstituted Ketones. Journal of the American Chemical Society, 135 (20). pp. 7442-7445. ISSN 0002-7863. doi:10.1021/ja402922w. https://resolver.caltech.edu/CaltechAUTHORS:20130709-110341676

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Abstract

The first enantioselective Ni-catalyzed reductive acyl cross-coupling has been developed. Treatment of acid chlorides and racemic secondary benzyl chlorides with a Ni^(II)/bis(oxazoline) catalyst in the presence of Mn^0 as a stoichiometric reductant generates acyclic α,α-disubstituted ketones in good yields and high enantioselectivity without requiring stoichiometric chiral auxiliaries or pregeneration of organometallic reagents. The mild, base-free reaction conditions are tolerant of a variety of functional groups on both coupling partners.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/ja402922wDOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja402922wPublisherArticle
ORCID:
AuthorORCID
Cherney, Alan H.0000-0001-7440-6634
Kadunce, Nathaniel T.0000-0002-6566-9851
Reisman, Sarah E.0000-0001-8244-9300
Additional Information:© 2013 American Chemical Society. Received: March 22, 2013 Published: May 1, 2013. We thank Prof. Brian Stoltz, Dr. Scott Virgil, and the Caltech Center for Catalysis and Chemical Synthesis for access to analytical equipment and Sigma-Aldrich for a kind donation of chemicals. Fellowship support was provided by the National Science Foundation (Graduate Research Fellowship, A.H.C., Grant No. DGE-1144469). S.E.R. is a fellow of the Alfred P. Sloan Foundation and a Camille Dreyfus Teacher-Scholar. Financial support from the California Institute of Technology, Amgen, and Novartis is gratefully acknowledged.
Funders:
Funding AgencyGrant Number
NSF Graduate Research FellowshipDGE-1144469
Alfred P. Sloan FoundationUNSPECIFIED
Camille and Henry Dreyfus FoundationUNSPECIFIED
CaltechUNSPECIFIED
AmgenUNSPECIFIED
NovartisUNSPECIFIED
Issue or Number:20
DOI:10.1021/ja402922w
Record Number:CaltechAUTHORS:20130709-110341676
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20130709-110341676
Official Citation:Catalytic Asymmetric Reductive Acyl Cross-Coupling: Synthesis of Enantioenriched Acyclic α,α-Disubstituted Ketones Alan H. Cherney, Nathaniel T. Kadunce, and Sarah E. Reisman Journal of the American Chemical Society 2013 135 (20), 7442-7445
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:39270
Collection:CaltechAUTHORS
Deposited By: Jason Perez
Deposited On:10 Jul 2013 18:40
Last Modified:09 Nov 2021 23:43

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