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Synthesis of Enantioenriched Allylic Silanes via Nickel-Catalyzed Reductive Cross-Coupling

Hofstra, Julie L. and Cherney, Alan H. and Ordner, Ciara M. and Reisman, Sarah E. (2018) Synthesis of Enantioenriched Allylic Silanes via Nickel-Catalyzed Reductive Cross-Coupling. Journal of the American Chemical Society, 140 (1). pp. 139-142. ISSN 0002-7863. http://resolver.caltech.edu/CaltechAUTHORS:20171205-112031343

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Abstract

An asymmetric Ni-catalyzed reductive cross-coupling has been developed to prepare enantioenriched allylic silanes. This enantioselective reductive alkenylation proceeds under mild conditions and exhibits good functional group tolerance. The chiral allylic silanes prepared here undergo a variety of stereospecific transformations, including intramolecular Hosomi-Sakurai reactions, to set vicinal stereogenic centers with excellent transfer of chirality.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://doi.org/10.1021/jacs.7b11707DOIArticle
http://pubs.acs.org/doi/10.1021/jacs.7b11707PublisherArticle
http://pubs.acs.org/doi/suppl/10.1021/jacs.7b11707PublisherSupporting Information
ORCID:
AuthorORCID
Reisman, Sarah E.0000-0001-8244-9300
Additional Information:© 2017 American Chemical Society. Received: November 3, 2017. Published: December 4, 2017. We thank Dr. Scott Virgil and the Caltech Center for Catalysis and Chemical Synthesis for access to analytical equipment. We also thank Dr. Michael K. Takase and Mr. Lawrence M. Henling for assistance with X-ray crystallography, as well as Dr. Mona Shahgholi and Naseem Torian for assistance with mass spectrometry measurements. Fellowship support was provided by the National Science Foundation (Graduate Research Fellowship, J.L.H., A.H.C., Grant No. DGE-1144469) and Caltech SURF program (Richard H. Cox and John Stauffer Fellowships, C.M.O.). S.E.R. is an American Cancer Society Research Scholar and Heritage Medical Research Institute Investigator. Financial support from the NIH (R35GM118191-01; GM111805-01) is gratefully acknowledged. The authors declare no competing financial interest.
Group:Heritage Medical Research Institute
Funders:
Funding AgencyGrant Number
NSF Graduate Research FellowshipDGE-1144469
Caltech Summer Undergraduate Research Fellowship (SURF)UNSPECIFIED
American Cancer SocietyUNSPECIFIED
Heritage Medical Research InstituteUNSPECIFIED
NIHR35GM118191-01
NIHGM111805-01
Record Number:CaltechAUTHORS:20171205-112031343
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20171205-112031343
Official Citation:Synthesis of Enantioenriched Allylic Silanes via Nickel-Catalyzed Reductive Cross-Coupling Julie L. Hofstra, Alan H. Cherney, Ciara M. Ordner, and Sarah E. Reisman Journal of the American Chemical Society 2018 140 (1), 139-142 DOI: 10.1021/jacs.7b11707
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:83692
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:08 Dec 2017 03:57
Last Modified:03 Feb 2018 00:38

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