Highly Active Au (I) Catalyst for the Intramolecular e xo-Hydrofunctionalization of Allenes with Carbon, Nitrogen, and Oxygen Nucleophiles

Z Zhang, C Liu, RE Kinder, X Han, H Qian…

Index: Zhang, Zhibin; Liu, Cong; Kinder, Robert E.; Han, Xiaoqing; Qian, Hua; Widenhoefer, Ross A. Journal of the American Chemical Society, 2006 , vol. 128, # 28 p. 9066 - 9073

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Citation Number: 368

Abstract

Reaction of benzyl (2, 2-diphenyl-4, 5-hexadienyl) carbamate (4) with a catalytic 1: 1 mixture of Au [P (t-Bu) 2 (o-biphenyl)] Cl (2) and AgOTf (5 mol%) in dioxane at 25° C for 45 min led to isolation of benzyl 4, 4-diphenyl-2-vinylpyrrolidine-1-carboxylate (5) in 95% yield. The Au (I)- catalyzed intramolecular hydroamination of N-allenyl carbamates tolerated substitution at the alkyl and allenyl carbon atoms and was effective for the formation of piperidine ...