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Paper | Special issue | Vol 101, No. 1, 2020, pp.195-208
Published online, 31st July, 2019
DOI: 10.3987/COM-19-S(F)13
Gold(I)-Catalyzed 10-endo-dig-Selective Cycloisomerization of N-(2-Anilinobenzyl)propargylamines

Mamoru Ito,* Daisuke Inoue, Asahi Takaki, Kyalo Stephen Kanyiva, and Takanori Shibata*

*Chemistry and Biochemistry, Advanced Research Center of Science and Engineering, Waseda University, 3-4-1 Okubo, Shinjuku-ku, Tokyo 169-8555, Japan

Abstract

The cationic gold(I)-catalyzed 10-endo-dig-selective cycloisomerization of N-(2-anilinobenzyl)propargylamine derivatives was developed. The reaction proceeded smoothly under mild conditions to give dibenzodiazecines. The catalytic construction of an entropically and enthalpically disfavored ten-membered ring was achieved by using a highly nucleophilic 3,5-dimethoxyanilino group as a reaction site.