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Gold(I)-Catalyzed Cyclization of Ene-Ynamide Carboxylates Involving 1,2-Group Migration: Synthesis of Functionalized
Mingduo Lu1, Jiaxiao Lv2, Wanjun Zheng2
1State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, P. R. China.
Abstract:
A gold-catalyzed cascade cyclization of ene-ynamides bearing a propargyl carboxylate moiety has been developed, which involves a 1,2-migration of the alkene substituent as a key step. The method provides an efficient route for the synthesis of functionalized 2-acylquinolines, with high selectivity favoring 1,2-aryl migration over 1,2-H or -alkyl migration. In addition, the nature of the propargylic substituent has a significant effect on the reaction outcome. When an aryl substituent is present, 2-indenyl-substituted indole is formed via a cyclopropyl gold carbene intermediate, leading to cleavage of the C═C bond in the ene-ynamide substrate.
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