Highly regio- and enantioselective conjugate addition of hydrazines to α,β-unsaturated imides

ORGN 724

Takahiro Soeta, Takahiro.Soeta@ndsu.edu and Mukund P. Sibi, Mukund.Sibi@ndsu.edu. Department of Chemistry, North Dakota State University, Ladd Hall, Fargo, ND 58105
Enantiomerically enriched pyrazolidinones have received attention as versatile chiral building blocks. Only one example for the synthesis of enantiomerically enriched pyrazolidinones via kinetic resolution of azomethine imines has been reported. However, kinetic resolution involves a significant disadvantage as half of the starting material is discarded. Herein, we wish to report a straightforward asymmetric synthesis of chiral 3-substituted-pyrazolidinones with high enantioselectivity in good yields via highly regio- and enantioselective addition of hydrazines to α,β-unsaturated imides. Details of the synthetic methodology and scope of the methodology will be presented