Application and utility of pyrazolidinone auxiliaries in enantioselective transformations

ORGN 721

Levi Stanley, levi.stanley@ndsu.edu and Mukund P. Sibi, Mukund.Sibi@ndsu.edu. Department of Chemistry, North Dakota State University, Ladd Hall, Fargo, ND 58105
We have previously reported the utility of pyrazolidinone auxiliaries in a number of enantioselective transformations including dipolar cycloadditions, Diels-Alder cycloadditions, and conjugate additions. Much of this past effort has focused on additions to β-substituted α,β-unsaturated pyrazolidinone imides. Currently, we are interested in expanding the use of pyrazolidinone auxiliaries to more challenging substrates and reactions. Enantioselective transformations of particular interest include: cycloadditions to alkynoates, exo-selective Diels-Alder reactions, and addition reactions to α-substituted α,β-unsaturated substrates. Results demonstrating the use of pyrazolidinone auxiliaries to address these areas of interest will be presented.