Abstract
Abstract The Generation of N-silylated azomethine ylides was achieved by the reaction of α-silylimidates and trifluorophenylsilane. The generated azomethine ylides can be regarded as synthetic equivalents of nitrile ylides since they have an alkoxy group which may serve as a leaving group. Cycloaddition with acetylenic or olefinic dipolarophiles proceeded smoothly to give pyrrole or pyrroline derivatives in good to excellent yields. For example, α-silylimidate 1 was treated with 1.2 equiv of trifluorophenylsilane in the presence of 1 equiv of dimethyl acetylenedicarboxylate to give pyrrole 2 in 97% yield. Furthermore, when starting with a secondary α-silylamide, the one-pot synthesis of N-unsubstituted azomethine ylides could be achieved by the successive treatment with alkylation and desilylation agents.
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