Gold-catalyzed intermolecular coupling of sulfonylacetylene with allyl ethers: [3,3]- and [1,3]-rearrangements

• Jungho Jun,
• Hyu-Suk Yeom,
• Jun-Hyun An and
• Seunghoon Shin

Beilstein J. Org. Chem. 2013, 9, 1724–1729, doi:10.3762/bjoc.9.198

• ]-rearrangement products through the formation of a tight ion–dipole pair. Keywords: gold catalysis; intermolecular coupling; [1,3]-rearrangement; [3,3]-sigmatropic rearrangement; sulfonylacetylene; Introduction Homogeneous gold catalysis has been established during the last decade as a prominent tool in

• was chosen as the optimal ligand (Table 1, entries 8–13). Further optimization with regard to reactants stoichiometry was conducted. An increased rate was observed when the amount of allyl ethers increased up to 3 equivalents. However, an increase in the amount of sulfonylacetylene (1) was less

• not undergo O-attack on the alkyne in the presence of Ag-catalyst [7]. With the above optimized conditions in hand, the scope of the carboalkoxylation of sulfonylacetylene was examined (Table 2). The alkoxy group in the ethers 2 had an impact on the efficiency of the current tandem carboalkoxylation