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Published July 17, 2013 | Accepted Version + Supplemental Material
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Highly Z‑Selective and Enantioselective Ring-Opening/Cross-Metathesis Catalyzed by a Resolved Stereogenic-at-Ru Complex

Hartung, John
Grubbs, Robert H. ORCID icon
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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.

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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August 19, 2023
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