Regioselective cycloadditions of N-protonated azomethine ylides and 2-azaallyl anions generated from N-(silylmethyl) thioimidates, synthetic equivalents of …

…, S Kanemasa, T Yamada, K Matsuda

Index: Tsuge, Otohiko; Kanemasa, Shuji; Yamada, Toshiaki; Matsuda, Koyo Journal of Organic Chemistry, 1987 , vol. 52, # 12 p. 2523 - 2530

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Citation Number: 62

Abstract

A water-induced-desilylation method and a direct-desilylation method have been applied to N-(silylmethyl) thioimidates to lead to the generation of N-protonated azomethine ylides and 2-azaallyl anions, respectively. These reactive intermediates are captured as cycloadducts to electron-deficient olefins, aldehydes, and ketones. The reactions with unsymmetrically substituted olefins are highly regioselective but with reverse selectivity. Regioisomeric 1- ...