Silyl group transfer in the cycloaddition reactions of silyl iminium salts derived from aryl-substituted oximes

A Padwa, WH Dent, AM Schoffstall…

Index: Padwa, Albert; Dent, William H.; Schoffstall, Allen M.; Yeske, Philip E. Journal of Organic Chemistry, 1989 , vol. 54, # 18 p. 4430 - 4437

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Citation Number: 15

Abstract

Reaction of the iminium salt derived from benzaldehyde oxime and (trimethylsily1) methyl triflate with cesium fluoride gives rise to azomethine ylides. Dipolar cycloaddition proceeded with complete stereospecificity with dimethyl fumarate and maleate. In sharp contrast, reaction of the salt with alkynes produces dipolar cycloadducts derived from nitrones. The different products encountered result from the operation of several competing reactions ...