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Modular Access to Substituted Azocanes via a Rhodium-Catalyzed Cycloaddition-Fragmentation Strategy.

Shaw MH, Croft RA, Whittingham WG, Bower JF - J. Am. Chem. Soc. (2015)

Bottom Line: 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.

View Article: PubMed Central - PubMed

Affiliation: †School of Chemistry, University of Bristol, Bristol, BS8 1TS, United Kingdom.

ABSTRACT
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.

No MeSH data available.


Related in: MedlinePlus

Tricyclic Systems via Pictet–SpenglerCyclizations
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sch2: Tricyclic Systems via Pictet–SpenglerCyclizations


Modular Access to Substituted Azocanes via a Rhodium-Catalyzed Cycloaddition-Fragmentation Strategy.

Shaw MH, Croft RA, Whittingham WG, Bower JF - J. Am. Chem. Soc. (2015)

Tricyclic Systems via Pictet–SpenglerCyclizations
© Copyright Policy
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4508204&req=5

sch2: Tricyclic Systems via Pictet–SpenglerCyclizations
Bottom Line: 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.

View Article: PubMed Central - PubMed

Affiliation: †School of Chemistry, University of Bristol, Bristol, BS8 1TS, United Kingdom.

ABSTRACT
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.

No MeSH data available.


Related in: MedlinePlus