Highly regio- and diastereoselective 1,3-dipolar cycloaddition reactions of nitrile ylides

ORGN 137

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
1,3-dipolar cycloadditions continue to serve as one of the most significant methods for the construction of five-membered heterocycles. Asymmetric cycloadditions of numerous 1,3-dipoles are well known. Enantioselective methods for cycloadditions with nitrile ylides have not been reported. Herein, we wish to report the first successful examples of highly regio- and diastereoselective addition of nitrile ylides to olefins bearing a chiral oxazolidinone to afford 3,4-dihydro-2H-pyrrole derivatives in moderate to good yields. Details of the synthetic methodology and the breadth and scope of the reaction will be presented.