Auxiliary Controlled Intramolecular 1,3-Dipolar Cycloaddition Reactions of Chiral Azomethine Ylides

1,3-Dipolar cycloaddition reactions of azomethine ylides play an important role in the synthesis of highly substituted pyrollidines which are found in the structures of many important natural products and pharmaceuticals . Using this chemistry, four chiral centers can be created in a single step. The asymmetric version of this reaction has been tried both with achiral azomethine ylides and chiral dipolarophiles as well as chiral azomethine ylides and achiral dipolarophiles. In the former case, different chiral auxiliaries were attached to the dipolarophiles and very good results (in terms of yield and stereoselectivity) were obtained. In the case of chiral azomethine ylides, although different chiral auxiliaries were attached to the precursors of the azomethine ylides, a truly general solution to this problem remains to be found. For this purpose, we used Oppolzer’s sultam as a recoverable chiral auxiliary and developed a very good method for the synthesis of stereodefined aziridine-2-carboxylic acid derivatives . We used these aziridines in intermolecular 1,3-dipolar cycloaddition reactions of chiral stabilized azomethine yields with electron deficient dipolarophiles for the synthesis of highly substituted pyrrolidines . We extended our method and synthesized aziridines that could be used in intramolecular 1,3-dipolar cycloaddition reactions of chiral stabilized azomethine ylides. These types of reaction are commonly used in the literature especially in relation to total synthesis . In this paper, the synthesis of these aziridines and the results of the intramolecular 1,3-dipolar cycloaddition reactions of azomethine ylides derived from their thermal ring opening are reported.