Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 138, Issue 20, Pages 6372-6375Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.6b02653
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Funding
- ONR [N000141410650]
- NIH [5R01M031332-27]
- NSF [CHE-1212767]
- CIHR
- Amgen
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1502616] Funding Source: National Science Foundation
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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.
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