title: Redox-triggered C-C coupling of diols and alkynes: synthesis of β,γ-unsaturated α-hydroxyketones and furans by ruthenium-catalyzed hydrohydroxyalkylation.
abstract: Direct ruthenium-catalyzed CC coupling of alkynes and vicinal diols to form β,γ-unsaturated ketones occurs with complete levels of regioselectivity and good to complete control over the alkene geometry. Exposure of the reaction products to substoichiometric quantities of p-toluenesulfonic acid induces cyclodehydration to form tetrasubstituted furans. These alkyne-diol hydrohydroxyalkylations contribute to a growing body of merged redox-construction events that bypass the use of premetalated reagents and, hence, stoichiometric quantities of metallic by-products.
authors.forename: Emma L
authors.initials: EL
authors.lastname: McInturff
authors.forename: Khoa D
authors.initials: KD
authors.lastname: Nguyen
authors.forename: Michael J
authors.initials: MJ
authors.lastname: Krische
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D005663:Furans / Q000138:chemical synthesis*; D007659:Ketones / Q000138:chemical synthesis*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D012428:Ruthenium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000480:Alkynes; D005663:Furans; D007659:Ketones; D012428:Ruthenium