Direct vinylation of glucose derivatives with acetylene

Catalytic Reactions of Acetylene: A Feedstock for the Chemical Industry Revisited

“…Unfortunately, a great number of these studies were reported in publications available only in the Russian language, making them less accessible to a substantial fraction of researchers, and thus, they have received less attention than they deserve. The reviews on the subject of acetylene reactions in basic media written by Trofimov and co-workers present an overview on this topic. ,, An interesting application of the vinylation of OH groups that has been recently reported uses sugars to give chiral compounds containing vinyl groups . These compounds might be useful for the synthesis of polymers presenting chiral functionality starting from readily available chiral materials.…”

Three-Component Reaction between Vinyl Ethers, Secondary Phosphines, and Elemental Selenium: One-Pot Synthesis of 1-(Alkoxy)ethyl and 1-(Aryloxy)ethyl Phosphinodiselenoates

“…The optically active vinyl ether 1j was obtained by direct vinylation of commercial 1,2:5,6-di-O-isopropylidene-a-D-glucofuranose with acetylene. 11 Diphenylphosphine (2d) was a commercial product (Aldrich). Secondary phosphines 2a-c were prepared by a known procedure from red phosphorus and styrene, 4-methoxystyrene, or 2-vinylfuran, respectively.…”

Hydroalkoxylation of alkynes by a nitroxyl containing alcohol, 4-hydroxy-2,2,6,6-tetramethylpiperidin-1-oxyl: synthesis of spin-labeled enol ethers

“…[25][26][27][28][29][30][31][32][33][34][35][36] Since the first synthesis of 4-vinyloxy-TEMPO, 24 no attempt to develop an expedient hydroalkoxylation of alkynes with 4-hydroxy-TEMPO has been undertaken. Meanwhile, having in mind that direct superbasecatalyzed hydroalkoxylation of alkynes with hydroxyl compounds has proved to be highly efficient, [37][38][39][40][41][42] we decided to revisit the vinylation of 4-hydroxy-TEMPO with various alkynes exploiting our expertise gained during the last decade.…”