Dual Gold Catalysis: A Novel Synthesis of Bicyclic and Tricyclic Pyrroles from N-Propargyl Ynamides

作者:Tokimizu Yusuke; Wieteck Marcel; Rudolph Matthias; Oishi Shinya; Fujii Nobutaka; Hashmi A Stephen K*; Ohno Hiroaki
来源:Organic Letters, 2015, 17(3): 604-607.
DOI:10.1021/ol503623m

摘要

Various N-propargyl ynamides were converted to bicylic and tricyclic pyrroles by the use of a cationic dual-activation gold catalyst. This reaction starts with the nucleophilic addition of a gold acetylide onto an ynamide triple bond at the beta-position of the nitrogen atom. Thus, gold vinylidene is formed, and then a second cyclization takes place. The formation of the gold vinylidene is indicated by the evidence that not only aryl ynamides but also alkyl ynamides undergo C-H activation in these reactions.

  • 出版日期2015-2-6