A catalytic enantioselective indium-mediated allylation of hydrazones

ORGN 548

Gregory R. Cook, Gregory.Cook@ndsu.edu, Robert Kargbo, robert.kargbo@ndsu.edu, and Bikash Maity, bdmaity@yahoo.com. Department of Chemistry and Molecular Biology, North Dakota State University, 1231 Albrecht Avenue, P.O. Box 5516, Fargo, ND 58105-5516
Over the last decade, allylindium complexes have emerged as mild and effective reagents for the allylation of carbonyl compounds. The application of chiral ligands to indium-mediated allylations has been an arduous challenge due to the low heterophilicity of the organoindium reagents. We have realized the asymmetric allylation of hydrazones utilizing allylindium and chiral additives. In this presentation we will demonstrate the enantioselective indium-mediated allylation of hydrazones affording homoallylic amines in high selectivity employing a catalytic amount of chiral additive. Our latest understanding of the factors controlling the selectivity, substrate scope and limitations will be presented.

 

Asymmetric Reactions and Syntheses
1:00 PM-5:00 PM, Wednesday, 31 August 2005 Washington DC Convention Center -- 201, Oral

Division of Organic Chemistry

The 230th ACS National Meeting, in Washington, DC, Aug 28-Sept 1, 2005