Configurationally stable carbanionic reagents for enantioselective synthesis

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With this renewal award, the Organic and Macromolecular Chemistry Program continues to support the work of Professor Paul R. Carlier of the Department of Chemistry, Virginia Tech. Professor Carlier will continue to develop new enantiopure group 1 and 2 organometallics that are configurationally stable at carbon within the time required for their generation and intermolecular reaction. He will also continue his investigations of enolates and enol ethers that are chiral and non-racemic solely by virtue of their conformation. These species will be valuable nucleophiles for the synthesis of pharmaceuticals. Furthermore, the studies of these species will increase our understanding of the structural features required to prevent facile racemization of C-chiral sp3-hybridized organometallics and conformationally chiral reactive intermediates.The improved understanding of configurational and conformational stability expected to result from this project should broadly impact the fields of natural product synthesis, pharmaceutical chemistry, and synthetic methodology development. Since stereochemical configuration represents a type of information, the insights gained here may one day prove useful in molecular electronics. The emphasis on integrating mechanistic and computational studies with new reaction discovery provides excellent training for undergraduates, Ph.D. students, and postdoctoral associates.