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Paper | Special issue | Vol 88, No. 2, 2014, pp.1039-1049
Published online, 14th August, 2013
DOI: 10.3987/COM-13-S(S)63
Lewis Acid Catalyzed Diastereoselective 1,3-Dipolar Cycloaddition between Diazoacetoacetate Enones and Azomethine Ylides

Phong M. Truong, Michael D. Mandler, Charles S. Shanahan, and Michael P. Doyle*

*Department of Chemistry and Biochemistry, University of Maryland, 7950 Baltimore Avenue, College Park, MD 20742, U.S.A.

Abstract

Silver acetate catalyzed 1,3-dipolar cycloaddition reactions of diazoacetoacetate enones and azomethine ylides produce tetrasubstituted pyrrolidines bearing a diazoacetoacetate functional array in excellent yields and diastereoselectivities. The installment of the diazoacetoacetate functional array allows access to diverse hetereocyclic scaffolds.