Unactivated Norbornenes in [3+2] Cycloadditions: Remarkably Stereocon- trolled Entry into Norbornane-Fused-Spirooxindolopyrrolidines, Spiro-1,3- in- dandionolylpyrrolidines and Spirooxindolopyrrolizidines

Abstract

1,3-dipolar cycloaddition reactions of azomethine ylides with unactivated norbornene dipolarophiles and a highly diastereoselective synthesis of the novel norbornane-fused spirooxindolopyrrolidines, spiroacenaphthylenolylpyrrolidines, spiro-1,3-indandionolylpyrrolidines, and spirooxindolopyrrolizidines having an array of stereocenters are reported. The stereoselective synthesis of spirooxindolopyrrolizidines with eight stereocenters was demonstrated. Single-crystal X-ray structural analyses were performed to unambiguously establish the structure and stereochemistry of the key products.