HETEROCYCLES

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■ 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.