Saturday, April 28, 2007

Gold(I)-Catalyzed Intramolecular Hydroamination of Alkenyl Carbamates


Xiaoqing Han, Ross A. Widenhoefer
Angewandte Chemie International Edition;
2006, 45, 1747-1749
DOI: 10.1002/anie.200600052

Summary: This paper describes the intramolecular gold(I)-catalyzed hydroamination of olefinic carbamates for the preparation of functionalized saturated nitrogen heterocycles. The products incorporate either five or six membered ring system via an exo-trig cyclization. This Au(I)-catalyzed reaction overcomes several limitations of the corresponding Pt-mediated annulation such as substrate scope and reaction temperature. Determination of the optimized conditions (ligand and solvent studies - 8 examples: 7-98% yield) plus 15 additional examples using the optimized conditions: 59-97% yield

No comments: