Stereogenic Organocopper Reagents

Clemson University, Clemson SC

Investigators

Abstract

The objective of this work is to understand and develop the reaction chemistry of stereogenic organocopper reagents. The scope of reactivity of these "chiral carbanions" will be explored; specifically a variety of alpha alkoxyalkyl cuprates and alpha amino alkyl cuprates will be prepared and the stereoselectivity of their vinylation, acylation, conjugate addition, and substitution reactions will be investigated. Asymmetric deprotonation and transmetallation will be used as routes to prepare these reagents and for any substrate where these routes might fail then stereogenic cuprates will be prepared by dynamic thermodynamic resolution. Efforts to determine the structures of the organocopper reagents and kinetics of reactions that provide the highest enantio- and diastereoselectivites will be undertaken. With this award, the Organic and Macromolecular Chemistry Program is supporting the research of Dr. R. Karl Dieter of the Department of Chemistry at Clemson University. Dr. Dieter will explore the reaction chemistry of stereochemically enriched organocopper reagents. The ability to form carbon-carbon bonds in molecules which are chiral (have two nonsuperimposable mirror images) and make only one of the two possible forms (a single enantiomer) is one of the most important problems facing the pharmaceutical industry today. When developed, Dr. Dieter's work could be applied to the synthesis of nitrogen and oxygen containing heterocycles with activities as antibacterial agents, CNS agents, and antiretroviral compounds. Students trained during the course of this work will gain skills needed by the pharmaceutical industry which now produces a number of single enantiomer compounds.