Stereochemical Studies in Allylmetal-Aldehyde, -Acetal and Aldol Reactions

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The Organic Synthesis Program supports the work of Scott Denmark, of the University of Illinois. Prof. Denmark's work involves examining how a reaction central to organic synthesis and biochemistry, the aldol condensation, can result in compounds with unique spatial orientations of atoms. The orientation in space of atoms can have profound effects on both chemical and biological behavior of molecules, and it is one of the challenges of modern organic chemists to understand how reactions result in these characteristics. The program has three objectives: (a) the examination of the factors controlling stereoselectivity of reactions of allylmetals with aldehydes and acetals, (b) the clarification of the nature of the intermediates in these reactions, and (c) the design, synthesis and testing of novel Lewis acids for their potential as chiral catalysts. The study involves extensive use of specific model compounds with unique stereochemical centers.