Regioselective transformation of alkynes into cyclic acetals and thioacetals with a gold(I) catalyst: comparison with Bronsted acid catalysts

Au(I) catalyzes the transformation of alkynes into cyclic acetals and thioacetals at much higher rate than Bronsted acids. The reaction appears to be general for a range of alkynes and diols or dithiols, which are efficiently transformed with high selectivities. One of the salient features of this reaction process is the high reactivity of the enol ether or enol thioether intermediates, which undergo a rapid isomerization reaction to afford the cyclic acetals or thioacetals, so that isolation or subsequent activation processes are not required. This type of reactions allows us to synthesize a series of fragrances. (C) 2008 Elsevier Ltd. All rights reserved.