The gold-catalyzed reactions of 2-alkynyl benzaldehydes 1   with acyclic or cyclic vinyl ethers afforded acetal-tethered dihydronaphthalene 2  , isochromene 3  and bicyclo[2.2.2]octane 4  under mild reaction conditions. These products contain interesting substructures that have been found in various biologically active compounds as well as natural products. In addition, a gold-catalyzed homo-dimerization of 2-phenylethynyl benzaldehyde 1a   was observed to yield separable diastereomeric products 5  . The scope and mechanistic insight for the formations of these interesting compounds will be discussed.

Gold-catalyzed annulations of 2-alkynyl benzaldehydes with vinyl ethers: Synthesis of dihydronaphthalene, isochromene, and bicyclo[2.2.2]octane derivatives

246th National Meeting (2013)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.