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High Trans Kinetic Selectivity in Ruthenium-Based Olefin Cross-Metathesis through Stereoretention

Johns, Adam M. and Ahmed, Tonia S. and Jackson, Bradford W. and Grubbs, Robert H. and Pederson, Richard L. (2016) High Trans Kinetic Selectivity in Ruthenium-Based Olefin Cross-Metathesis through Stereoretention. Organic Letters, 18 (4). pp. 772-775. ISSN 1523-7060. doi:10.1021/acs.orglett.6b00031. https://resolver.caltech.edu/CaltechAUTHORS:20160208-104033108

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Abstract

The first kinetically controlled, highly trans-selective (>98%) olefin cross-metathesis reaction is demonstrated using Ru-based catalysts. Reactions with either trans or cis olefins afford products with highly trans or cis stereochemistry, respectively. This E-selective olefin cross-metathesis is shown to occur between two trans olefins and between a trans olefin and a terminal olefin. Additionally, new stereoretentive catalysts have been synthesized for improved reactivity.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/acs.orglett.6b00031DOIArticle
http://pubs.acs.org/doi/abs/10.1021/acs.orglett.6b00031PublisherArticle
http://pubs.acs.org/doi/suppl/10.1021/acs.orglett.6b00031PublisherSupporting Information
ORCID:
AuthorORCID
Grubbs, Robert H.0000-0002-0057-7817
Additional Information:© 2016 American Chemical Society. Received: January 5, 2016. Publication Date (Web): February 3, 2016. Financial support from the Office of Naval Research (N00014-14-1-0650) and the NSF (CHE-1502616) is acknowledged. T.S.A. acknowledges support from the National Science Foundation for a Graduate Research Fellowship. Any opinion, findings, and conclusions or recommendations expressed in this material are those of the authors and do not necessarily reflect the views of the National Science Foundation. The authors declare no competing financial interest.
Funders:
Funding AgencyGrant Number
Office of Naval Research (ONR)N00014-14-1-0650
NSFCHE-1502616
NSF Graduate Research FellowshipUNSPECIFIED
Issue or Number:4
DOI:10.1021/acs.orglett.6b00031
Record Number:CaltechAUTHORS:20160208-104033108
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20160208-104033108
Official Citation:High Trans Kinetic Selectivity in Ruthenium-Based Olefin Cross-Metathesis through Stereoretention Adam M. Johns, Tonia S. Ahmed, Bradford W. Jackson, Robert H. Grubbs, and Richard L. Pederson Organic Letters 2016 18 (4), 772-775 DOI: 10.1021/acs.orglett.6b00031
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:64300
Collection:CaltechAUTHORS
Deposited By: George Porter
Deposited On:08 Feb 2016 21:07
Last Modified:10 Nov 2021 23:28

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