Design, Synthesis and Applications of Chiral N-Heterocyclic and Organometallic Reagents

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Many organic molecules can exist in left or right-handed forms. While these molecules are identical in all respects except that they are mirror images of each other, they can have profoundly different physiological properties. The public became aware of the "handedness" in organic molecules in the 1960's when the drug thalidomide was given as a mixture of left and right-handed forms to pregnant women to combat morning sickness. Although the right-handed form of the drug was beneficial, the left-handed form caused severe birth defects in children, and thalidomide was quickly banned. Subsequently, extensive efforts were placed on synthesizing organic molecules selectively in purely left or right-handed forms by using "handed" catalysts; these efforts continue today. The proposed research outlines a new class of "handed" molecules which until recently could not be easily prepared, but for which there are exciting prospects for new catalyst development. It is anticipated that the new catalysts will offer opportunities to develop new chemical transformations with which to selectively make handed molecules, of which one of the many potential benefits includes the preparation of safer drugs.