Published July 17, 2013
| Version Accepted Version + Supplemental Material
Journal Article
Open
Highly Z‑Selective and Enantioselective Ring-Opening/Cross-Metathesis Catalyzed by a Resolved Stereogenic-at-Ru Complex
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.
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.Attached Files
Accepted Version - nihms502334.pdf
Supplemental Material - ja4046422_si_001.pdf
Supplemental Material - ja4046422_si_002.pdf
Supplemental Material - ja4046422_si_003.cif
Supplemental Material - ja4046422_si_004.cif
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ja4046422_si_001.pdf
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Additional details
Identifiers
- PMCID
- PMC3826570
- Eprint ID
- 41537
- DOI
- 10.1021/ja4046422
- Resolver ID
- CaltechAUTHORS:20130930-074857572
Funding
- NIH
- 5R01GM031332-27
- NSF
- CHE-0639094
Dates
- Created
-
2013-09-30Created from EPrint's datestamp field
- Updated
-
2021-11-10Created from EPrint's last_modified field