Palladium-catalyzed intramolecular addition of amines to acetylenes. Synthesis of cyclic imines

Y Fukuda, S Matsubara, K Utimoto

文献索引：Fukuda, Yukitoshi; Matsubara, Seijiro; Utimoto, Kiitiro Journal of Organic Chemistry, 1991 , vol. 56, # 20 p. 5812 - 5816

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被引用次数: 70

摘要

Intramolecular aminopalladation of alkynylamines gave intermediary alkenylpalladium compounds that hydrolyzed and isomerized to thermodynamically stable cyclic imines. Treatment of 3-alkynylamines with a catalytic amount of PdC1z (MeCN) z gave exclusively 1- pyrrolines in good yields; 5-alkynylamines afforded 2, 3, 4, 5-tetrahydropyidines selectively. Treatment of 4-alkynylamines with Pd (I1) afforded mixtures of both 5-and 6-membered ...