Proline Hydantoin Derivatives as Dual Purpose Chiral Auxiliary and Chiral Catalyst Precursors

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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 chemical and 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; these efforts continue today. The proposed research outlines the development of an easy to make molecular fragment that, when incorporated into specific molecules, offers many opportunities for the synthesis of challenging to make "handed" molecules, either directly, or by its conversion into catalysts. It is anticipated this new fragment will offer opportunities to develop new chemical transformations, of which one of the many potential benefits includes the preparation of safer drugs.