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The PRF supported research conducted within my laboratory at Northwestern University has led to the development of several highly useful synthetic methods centered on the use of N-allyllhydrazones as readily prepared compounds that can undergo a diverse array of powerful reactions. Specifically, the research has provided a novel method for incorporating chlorine into petrochemical feedstocks by way of a completely unprecedented tandem carbon–carbon and carbon–chlorine bond forming process (J. Am. Chem. Soc. 2008).  We have also developed an efficient one-pot procedure for converting N-allylhydrazones into stereodefined dienes, a class of highly useful intermediates for synthesis (Org. Lett. 2009).

Our current focus is directed towards inventive strategies for i) The sp³–sp³ coupling of unactivated carbon atoms; ii) Iterative asymmetric synthesis and catalysis; and iii) Complexity generating cascade sequences.  To this end, we have established a triflimide-catalyzed sigmatropic rearrangement of N-allylhydrazones that generates a new carbon–carbon bond and will allow for complex molecule synthesis along non-traditional pathways.  This work also lays the foundation for our ongoing efforts in asymmetric catalysis.  A trait shared by all of these hydrazone-based transformations is that the products do not contain an obvious retron for the reaction that produced them.  Such transformations may be considered to be 'traceless' in the sense that the functionality in the starting material that allowed the reaction to proceed is no longer present in the product.  The development and application of such traceless rearrangements to complex molecule synthesis will have a significant impact in producing concise syntheses with minimal post-reaction manipulation. In addition, hydrazone formation and subsequent rearrangement is a thermodynamically favorable process driven by the extrusion of water and dinitrogen, which will ensure a high level of efficiency for each transformation