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Highly Z‑Selective and Enantioselective Ring-Opening/Cross-Metathesis Catalyzed by a Resolved Stereogenic-at-Ru Complex

Hartung, John and Grubbs, Robert H. (2013) Highly Z‑Selective and Enantioselective Ring-Opening/Cross-Metathesis Catalyzed by a Resolved Stereogenic-at-Ru Complex. Journal of the American Chemical Society, 135 (28). pp. 10183-10185. ISSN 0002-7863. PMCID PMC3826570. doi:10.1021/ja4046422. https://resolver.caltech.edu/CaltechAUTHORS:20130930-074857572

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Abstract

The synthesis of a ruthenium complex that catalyzes Z-selective (up to 98% Z) asymmetric ring-opening/cross-metathesis with high enantioselectivity (up to 95% ee) is reported. The synthesis of the catalyst features the resolution of a chelating N-heterocyclic carbene complex by ligand substitution with a chiral carboxylate.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/ja4046422DOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja4046422PublisherArticle
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3826570/PubMed CentralArticle
ORCID:
AuthorORCID
Grubbs, Robert H.0000-0002-0057-7817
Additional Information:© 2013 American Chemical Society. Received: May 8, 2013. Published: July 3, 2013. This work was financially supported by the NIH (5R01GM031332-27 to R.H.G.). The authors thank Mr. L. M. Henling for X-ray crystallography. The Bruker KAPPA APEXII X-ray diffractometer was purchased via an NSF CRIF:MU Award to the California Institute of Technology (CHE-0639094). The authors also thank Materia, Inc. for its donation of metathesis catalysts and Drs. Daryl Allen (Materia, Inc.) and Scott Virgil (Caltech Center for Catalysis and Chemical Synthesis) for helpful advice.
Funders:
Funding AgencyGrant Number
NIH5R01GM031332-27
NSFCHE-0639094
Issue or Number:28
PubMed Central ID:PMC3826570
DOI:10.1021/ja4046422
Record Number:CaltechAUTHORS:20130930-074857572
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20130930-074857572
Official Citation:Highly Z-Selective and Enantioselective Ring-Opening/Cross-Metathesis Catalyzed by a Resolved Stereogenic-at-Ru Complex John Hartung and Robert H. Grubbs Journal of the American Chemical Society 2013 135 (28), 10183-10185
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:41537
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:30 Sep 2013 16:21
Last Modified:10 Nov 2021 04:31

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