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Synthesis

An Alkene Carboamination

Organic Synthesis: Rhodium-catalyzed reaction stereospecifically forms a C–C bond and a C–N bond across a C=C bond

by Bethany Halford
October 26, 2015 | APPEARED IN VOLUME 93, ISSUE 42

Looking to turn simple alkenes into more complex molecules, chemists at Colorado State University report a stereospecific carboamination of C=C bonds. The reaction provides a new way to synthesize functionalized amines, which are often components of biologically important molecules. The rhodium-catalyzed reaction (example shown), developed by Tomislav Rovis and Tiffany Piou, adds a C–C bond and a C–N bond across an alkene’s double bond (Nature 2015, DOI: 10.1038/nature15691). Enoxyphthalimides serve as both the carbon and the nitrogen source in the intermolecular transformation. The reaction takes place in a syn fashion with both new bonds forming on the same side of the alkene. Developing a bulky cyclopentadienyl ligand for rhodium and using methanol as a solvent proved critical to getting the reaction to work. The team now has its sights set on an asymmetric version of the reaction.

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