Highly enantioselective indium-mediated crotylation of aliphatic hydrazones

ORGN 390

Gregory R. Cook, Gregory.Cook@ndsu.edu, Robert Kargbo, robert.kargbo@ndsu.edu, and Yoko Takahashi, yoko.takahashi@ndsu.edu. Department of Chemistry and Molecular Biology, North Dakota State University, 1231 Albrecht Avenue, P.O. Box 5516, Fargo, ND 58105-5516
Research into the addition of allylindium reagents to imines and their derivatives continues to proceed unabated - a consequence of the fact that these reactions are found to be very stereoselective and the resulting homoallylic amine products have proven to be valuable intermediates for organic synthesis. We have developed a robust methodology for the crotylation and allylation of aliphatic hydrazone derived from aliphatic aldehydes and ketones. These are classes of substrates that typically undergo reactions with lower efficiency and dismal asymmetric induction relative to aromatic analogues. Results of our investigations show the development of a highly efficient and enantioselective addition to aliphatic hydrazones. Details of these and related reactions will be presented.