Enantioselective synthesis of a chiral nitrogen-doped buckybowl

Tan, Q. et al. Enantioselective synthesis of a chiral nitrogen-doped buckybowl. Nat. Commun. 3:891 doi: 10.1038/ncomms1896 (2012).


http://www.nature.com/ncomms/journal/v3/n6/full/ncomms1896.html

The authors synthesized triazasumanene enantioselectively. They found that the incorporation of the three nitrogen atoms in the bowl increased the bowl depth relative to the all-carbon sumanene. This increase in depth also increased the energy barrier to inversion of the bowls. Sumanene undergoes rapid bowl inversion at room temperature, causing racemization. However, triazasumanene only shows any enantiomeric conversion after heating at 200 degrees for 12 hours.