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Nickel-Catalyzed Asymmetric Reductive Cross-Coupling Between Vinyl and Benzyl Electrophiles

Cherney, Alan H. and Reisman, Sarah E. (2014) Nickel-Catalyzed Asymmetric Reductive Cross-Coupling Between Vinyl and Benzyl Electrophiles. Journal of the American Chemical Society, 136 (41). pp. 14365-14368. ISSN 0002-7863. PMCID PMC4210114. doi:10.1021/ja508067c. https://resolver.caltech.edu/CaltechAUTHORS:20141007-155137202

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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.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/ja508067cDOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja508067cPublisherArticle
http://pubs.acs.org/doi/suppl/10.1021/ja508067cPublisherSupporting Information
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4210114/PubMed CentralArticle
ORCID:
AuthorORCID
Cherney, Alan H.0000-0001-7440-6634
Reisman, Sarah E.0000-0001-8244-9300
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.
Funders:
Funding AgencyGrant Number
NSF Graduate Research FellowshipDGE-1144469
American Chemical SocietyUNSPECIFIED
AmgenUNSPECIFIED
Alfred P. Sloan FoundationUNSPECIFIED
Camille and Henry Dreyfus FoundationUNSPECIFIED
American Cancer SocietyUNSPECIFIED
NIHGM111805-01
NovartisUNSPECIFIED
DuPontUNSPECIFIED
Eli LillyUNSPECIFIED
Issue or Number:41
PubMed Central ID:PMC4210114
DOI:10.1021/ja508067c
Record Number:CaltechAUTHORS:20141007-155137202
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20141007-155137202
Official Citation:Nickel-Catalyzed Asymmetric Reductive Cross-Coupling Between Vinyl and Benzyl Electrophiles Alan H. Cherney and Sarah E. Reisman Journal of the American Chemical Society 2014 136 (41), 14365-14368
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:50246
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:09 Oct 2014 21:45
Last Modified:10 Nov 2021 18:53

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