Lewis acid-catalyzed ring-opening reactions of semicyclic N, O-acetals possessing an exocyclic nitrogen atom: mechanistic aspect and application to piperidine …

…, H Hagio, R Hirabayashi, S Kobayashi

文献索引：Sugiura; Hagio; Hirabayashi; Kobayashi Journal of the American Chemical Society, 2001 , vol. 123, # 50 p. 12510 - 12517

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被引用次数: 87

摘要

Ring-opening reactions of semicyclic N, O-acetals possessing an exocyclic nitrogen atom with silicon-based nucleophiles (silyl enol ethers, ketene silyl acetals, allylic silanes, and trimethylsilyl cyanide) were systematically studied for the first time. It was found that the reactions were effectively catalyzed by a Lewis acid, trimethylsilyl trifluoromethanesulfonate (TMSOTf), to afford 1, 4-and 1, 5-amino alcohols in high yields. In reactions of 3-oxygen ...