1. Enantioselective Dearomatization Agents Based on Chiral C2-Symmetric Ligands
Joseph M. Keane, Department of Chemistry, Muhlenberg College, Allentown, PA
Inexpensive aromatic molecules such as naphthalene and toluene are potentially very useful starting materials for pharmaceutical syntheses, but their chemistry is currently severely limited by the stability of the aromatic core. One way to overcome this stability is through the interaction of aromatic molecules with very electron-rich metal centers. In this way, a myriad of novel transformations of aromatics have been demonstrated. One aspect of this chemistry that remains largely undeveloped is reactions of aromatics that occur with control of the three-dimensional shape of the reaction products. To this end, we have been developing a series of molybdenum and tungsten compounds with well-defined shapes about the metal centers. It is our hope to develop such a compound that will interact with aromatic molecules in a very specific geometrical arrangement, such that further reaction of the aromatics lead to products having exclusively one three-dimensional shape. The series of reactions below illustrates one of our recent approaches to the development of such a compound.