Journal
ORGANIC LETTERS
Volume 14, Issue 12, Pages 2956-2959Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol301212j
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Funding
- University of Crete of the NSRF
- European Union
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Gold nanoparticles supported on TiO2 (1.2 mol %) catalyze, for the first time under heterogeneous conditions, the cycloisomerization of a series of 1,6-enynes in high yields. In several cases, the product selectivity differs significantly as compared to homogeneous Au(I)-catalysis. Based on product analysis and stereoisotopic studies it is proposed that the major or exclusive pathway involves a 5-exo cyclization mode to form stereoselectively gold cyclopropyl carbenes that undergo a single cleavage pathway, in contrast to homogeneous Au-catalysis where the double cleavage pathway operates substantially.
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