Novel Stable Chiral Ligation for Asymmetric Organoborane Conversions via 10-Substituted-9-borabicyclo[3.3.2]decanes

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The objectives of this work involve several aspects of organoboron chemistry. Professor Soderquist and his group will first prepare a number of chiral allyl, crotyl, allenyl, and alkynyl boron reagents which contain the 9-borabicyclo[3.3.2]decane framework. The allyl, crotyl, and allenyl reagents will be utilized in asymmetric addition reactions to prochiral aldehydes and ketones. The chiral alkynyl organoboron reagents will be used in asymmetric conjugate addition reactions to enones. Boron NMR will be used to assess the stereoselectivities of these addition reactions. 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. Dr. Stewart will work on the development of organoboron reagents capable of effecting a number of chemical reactions. This group will explore stereoselective addition reactions using molecules containing ketones and aldehydes as substrates. These addition reactions produce molecules which are chiral (have two nonsuperimposable mirror images) and make only one of the two possible forms (a single enantiomer). Development of this family of reactions is one of the most important problems facing the pharmaceutical industry today. Students trained during the course of this work will gain skills needed by the pharmaceutical and speciality chemicals industries which now produces a number of single enantiomer compounds.