Tandem Olefin Metathesis/Oxidative Cyclization: Synthesis of Tetrahydrofuran Diols from Simple Olefins
- Creators
- Dornan, Peter K.
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Lee, Daniel
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Grubbs, Robert H.
Abstract
A tandem olefin metathesis/oxidative cyclization has been developed to synthesize 2,5-disubstituted tetrahydrofuran (THF) diols in a stereocontrolled fashion from simple olefin precursors. The ruthenium metathesis catalyst is converted into an oxidation catalyst in the second step and is thus responsible for both catalytic steps. The stereochemistry of the 1,5-diene intermediate can be controlled through the choice of catalyst and the type of metathesis conducted. This olefin stereochemistry then controls the THF diol stereochemistry through a highly stereospecific oxidative cyclization.
Additional Information
© 2016 American Chemical Society. Received: March 11, 2016. Publication Date (Web): April 30, 2016. This work was financially supported by the ONR (N000141410650), the NIH (5R01M031332-27), and the NSF (CHE-1212767). P.K.D. is grateful to the CIHR for a postodoctoral fellowship, and D.L. thanks the Amgen Scholar Program for a fellowship. L. M. Henling and M. Takase are thanked for X-ray crystallography. NMR spectra were obtained using instruments supported by the NIH (RR027690). Dr. Noah Fine Nathel, Dr. Patrick Montgomery, Dr. Daniel Ziegler, and Dr. Zachary Wickens are thanked for helpful discussions. Materia, Inc. is thanked for the donation of metathesis catalysts. he authors declare no competing financial interest.Attached Files
Accepted Version - nihms-813235.pdf
Supplemental Material - ja6b02653_si_001.pdf
Supplemental Material - ja6b02653_si_002.cif
Supplemental Material - ja6b02653_si_003.cif
Files
Additional details
- PMCID
- PMC5030111
- Eprint ID
- 67257
- Resolver ID
- CaltechAUTHORS:20160523-112835897
- N000141410650
- Office of Naval Research (ONR)
- 5R01M031332-27
- NIH
- RR027690
- NIH
- Created
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2016-05-23Created from EPrint's datestamp field
- Updated
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2022-04-27Created from EPrint's last_modified field