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Molecular Manipulations of Symmetry

Researchers have studied the effect of concentration on the activity and selectivity in a zirconium-catalyzed hydroamination reaction.  In this important reaction for the efficient and atom economical synthesis of valuable amine compounds, the nitrogen-hydrogen bond adds across a carbon double bond to give a new nitrogen-carbon bond.  Varying concentrations allows for the systematic tuning of a homogeneous 3D environment, impacting the selectivity. Selective amine synthesis is important, because although some molecules may look very similar (for instance, they are a mirror image of each other or enantiomers), their slightly different arrangements impact chemical function.  The molecular configuration of preferred molecular architecture is controlled by the concentration of the reaction medium, with one configuration favored under concentrated conditions and the other favored under dilute conditions.  Researchers were able to break molecular symmetry and then select the rearrangement pathway to yield the desired chemical architecture.  The results are a step on the pathway to designing systems where a molecularly engineered environment positively affects catalytic activity and selectivity, ultimately providing scientists with ways to systematically create more complex molecules.

Highlight Date: 
Monday, June 8, 2015
Article Title: 

Zirconium-Catalyzed Desymmetrization of Aminodialkenes and Aminodialkynes through Enantioselective Hydroamination

Kuntal Manna, Naresh Eedugurala, and Aaron D. Sadow
Article Link: 
Journal Name: 
Journal of the American Chemical Society
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