Autotandem catalysis: synthesis of pyrroles by gold-catalyzed cascade reaction
Hirofumi Ueda1, Minami Yamaguchi, Hiroshi Kameya
1Graduate School of Pharmaceutical Sciences, Tohoku University , Aoba 6-3, Aramaki, Aoba-ku, Sendai 980-8578, Japan.
Abstract:
A novel synthesis of substituted pyrroles by a gold(I)-catalyzed cascade reaction has been developed. The reaction proceeded with an autotandem catalysis consisting of an initial addition of gold-acetylide to an acetal moiety and was followed by gold-catalyzed 5-endo-dig cyclization and aromatization. Gold catalysts play a dual role in activating nucleophilicity or electrophilicity of terminal acetylenes by forming gold-acetylides or by π-coordination. The formal (3 + 2) annulation of two components provided a variety of substituted pyrroles in a modular fashion.
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