"The Development of Chiral Phosphoric-Acid Catalyzed Process"

ABSTRACT:
Antilla Group Research at The University of South Florida

Significant portions of important molecules involved in the biochemistry of life have "handedness," i.e. they are primarily found in one nonsuperimposible mirror image form. Additionally, the majority of drugs and drug candidates also have handedness (chirality) and all stereoisomers of these compounds are normally synthesized and evaluated for biological activity. Due to the chirality of nature, the mirror image forms of drug candidates can have vastly differing biological affects. One approach to the synthesis of chiral molecules that is growing steadily in usage is the application of versatile, stereoselective catalytic methodology in key steps where stereocontrol is required.

Organocatalysis, the use of small organic (non-metal based) molecules as catalysts is an attractive alternative to traditional metal-based catalysis. This approach has found a number of recent successes and the continued evaluation of organocatalytic-based chemistry is clearly a worthwhile endeavor. Since 2004 the use of chiral phosphoric acid-based organocatalysis has been shown to provide for excellent stereoselectivity in a growing number of reactions. Our efforts have been involved in the development of new methodology where chiral phosphoric acids can be applied stereoselectively. The aims of our research has involved the design, analysis, and refinement of a number of new reactions whereby chiral phosphoric acids can be efficient, stereoselective catalysts. The potential health-related utility of the newly created chiral products represents a long-term goal of the research.