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Synfacts 2009(10): 1097-1097  
DOI: 10.1055/s-0029-1217925
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart ˙ New York

Gold-Catalyzed Formation of Functionalized Carbocyclic Cages

Contributor(s): Timothy M. Swager, Jason R. Cox
S. M. Kim, J. H. Park, Y. K. Kang*, Y. K. Chung*
Seoul National University, Korea
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Publication History

Publication Date:
22 September 2009 (online)

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Significance

The authors report the use of gold NHC catalysis to transform N-tethered 1,5-bis­allenes to 6,7-dimethylene-3-azabicyclo[3.1.1]-heptanes. The reactions proceed at 75 ˚C with 5 mol% catalyst loading to give the products in high yields (74-98%). The reaction is effective on a number of 1,5-bisallene substrates to afford products that can undergo further derivatization at the olefins.