Published October 15, 2014
| Supplemental Material + Published
Journal Article
Open
Nickel-Catalyzed Asymmetric Reductive Cross-Coupling Between Vinyl and Benzyl Electrophiles
- Creators
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Cherney, Alan H.
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Reisman, Sarah E.
Abstract
A Ni-catalyzed asymmetric reductive cross-coupling between vinyl bromides and benzyl chlorides has been developed. This method provides direct access to enantioenriched products bearing aryl-substituted tertiary allylic stereogenic centers from simple, stable starting materials. A broad substrate scope is achieved under mild reaction conditions that preclude the pregeneration of organometallic reagents and the regioselectivity issues commonly associated with asymmetric allylic arylation.
Additional Information
© 2014 American Chemical Society. ACS AuthorChoice - This is an open access article published under an ACS AuthorChoice License, which permits copying and redistribution of the article or any adaptations for non-commercial purposes. Received: August 6, 2014. Publication Date (Web): September 22, 2014. We thank Prof. Brian Stoltz, Dr. Scott Virgil, and the Caltech Center for Catalysis and Chemical Synthesis for access to analytical equipment. Fellowship support was provided by the National Science Foundation (Graduate Research Fellowship, A.H.C., grant no. DGE-1144469) and the ACS Division of Organic Chemistry (A.H.C., sponsored by Amgen). S.E.R. is a fellow of the Alfred P. Sloan Foundation, a Camille Dreyfus Teacher-Scholar, and an American Cancer Society Research Scholar. Financial support from NIH (GM111805-01), Amgen, Novartis, DuPont, and Eli Lilly is gratefully acknowledged.Attached Files
Published - ja508067c.pdf
Supplemental Material - ja508067c_si_001.pdf
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Additional details
- PMCID
- PMC4210114
- Eprint ID
- 50246
- Resolver ID
- CaltechAUTHORS:20141007-155137202
- DGE-1144469
- NSF Graduate Research Fellowship
- American Chemical Society
- Amgen
- Alfred P. Sloan Foundation
- Camille and Henry Dreyfus Foundation
- American Cancer Society
- GM111805-01
- NIH
- Novartis
- DuPont
- Eli Lilly
- Created
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2014-10-09Created from EPrint's datestamp field
- Updated
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2021-11-10Created from EPrint's last_modified field