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Paper | Special issue | Vol 42, No. 1, 1996, pp.385-395
Published online, 1st January, 1970
DOI: 10.3987/COM-95-S50
New Anionic Cyclization of 4- and 5-Alkynylamines: Synthesis of 2-Benzylidene Pyrrolidines and Piperidines

Masao Tokuda, Hirotake Fujita, Makoto Nitta, and Hiroshi Suginome

*Division of Molecular Chemistry, Graduate School of Engineering, Hokkaido University, Sapporo 060-8628, Japan


Treatment of 4- and 5-alkynylamines with 0.5-1.2 equiv. of butyllithium brought about a facile anionic cyclization, giving the corresponding enamine pyrrolidines and piperidines having an exo double bond in high yields. Treatment of 4-alkynamides with lithium aluminum hydride also gave the similar enamine pyrrolidines in high yields.