Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 137, Issue 25, Pages 8054-8057Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.5b05215
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Funding
- European Research Council via the European Union's Horizon Programme (ERC) [639594 CatHet]
- EPSRC [EP/G036764/1]
- Syngenta
- Royal Society
- EPSRC [EP/K03927X/1] Funding Source: UKRI
- Engineering and Physical Sciences Research Council [981180, EP/K03927X/1] Funding Source: researchfish
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A short entry to substituted azocanes by a Rh-catalyzed cycloaddition-fragmentation process is described. Specifically, exposure of diverse N-cyclopropylacrylamides to phosphine-ligated cationic Rh(I) catalyst systems under a CO atmosphere enables the directed generation of rhodacyclopentanone intermediates. Subsequent insertion of the alkene component is followed by fragmentation to give the heterocyclic target. Stereochemical studies show, for the first time, that alkene insertion into rhodacyclopentanones can be reversible.
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