Synthetic application of cyanoaminosilanes as azomethine ylide equivalents

…, YY Chen, W Dent, H Nimmesgern

Index: Padwa, Albert; Chen, Yon-Yih; Dent, William; Nimmesgern, Hildegard Journal of Organic Chemistry, 1985 , vol. 50, # 21 p. 4006 - 4014

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Citation Number: 83

Abstract

A series of a-cyanoaminosilanes have been found to act as azomethine ylide equivalents. Treatment of these compounds with silver fluoride in the presence of electron-deficient alkynes and olefins gives substituted pyrroles and pyrrolidines in high yield. It was found that N-benzyl-N-(cyanomethyl)-N-[(trimethylsily1) methyllamine undergoes stereospecific cycloaddition with dimethyl fumarate and maleate. The stereospecificity of the reaction is ...