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Autotandem Catalysis: Synthesis of Pyrroles by Gold-Catalyzed Cascade Reaction

Hirofumi Ueda, Minami Yamaguchi, Hiroshi Kameya, Kenji Sugimoto and Hidetoshi Tokuyama*

*Graduate School of Pharmaceutical Sciences, Tohoku University, Aoba 6-3, Aramaki, Aoba-ku, Sendai 980-8578, Japan, Email: tokuyamamail.pharm.tohoku.ac.jp

H. Ueda, M. Yamaguchi, H. Kameya, K. Sugimoto, H. Tokuyama, Org. Lett., 2014, 16, 4948-4951.

DOI: 10.1021/ol5024695 (free Supporting Information)


Abstract

A synthesis of substituted pyrroles by a gold(I)-catalyzed cascade reaction proceeds via an autotandem catalysis consisting of an initial addition of gold-acetylide to an acetal moiety followed by gold-catalyzed 5-endo-dig cyclization and aromatization. This formal (3 + 2) annulation of two components provides various substituted pyrroles in a modular fashion.

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Key Words

Pyrroles


ID: J54-Y2014