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.
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| 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. | ||||||||||||||
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| 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: | INVALID USER | ||||||||||||||
| Deposited On: | 10 Jul 2013 18:40 | ||||||||||||||
| Last Modified: | 09 Nov 2021 23:43 |
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