Stable Chiral Ligation for Asymmetric Organoborane Conversions via 10-(Trimethylsilyl)-9-borabicycloÔ3.3.2Òdecanes

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The objective of the proposed research is to develop a new class of organoboron chiral auxiliaries for use in organic synthesis. The reagent is derived from pinene, a plentiful and inexpensive "chiral pool" material. Potential applications to a variety of asymmetric reactions will be explored, including the aldol, allylation and hydroboration reactions. Other possible applications to be explored include asymmetric alkynylborations of aldehydes, which give optically active propargyl alcohols. With this award, the Organic and Macromolecular Chemistry Program is supporting the research of Dr. John A. Soderquist of the Department of Chemistry at the University of Puerto Rico, Rio Piedras. Professor Soderquist's research is in the important area of producing chiral molecules, which are ever-important as pharmaceutical agents. The method that is employed by Dr. Soderquist uses pinene as a natural chiral template, and boron chemistry to mediate the transfer of chirality from the pinene into the molecule that is being formed.