title: Bifunctionalized Allenes. Part XVI. Synthesis of 3-Phosphoryl-2,5-dihydrofurans by Coinage Metal-Catalyzed Cyclo-isomerization of Phosphorylated α-Hydroxyallenes.
abstract: Phosphorylated α-hydroxyallenes 1 and 2 were smoothly converted into the corresponding 2,5-dihydrofurans 3 and 4 in an 5-endo-trig cycloisomerization reaction by using 5 mol % of coinage metal salts as catalyst. Experimental conditions such as the type of the solvent, the reaction temperature, the mol % and the type of the catalyst were optimized. This mild and efficient cyclization method can be applied to dimethyl 1-hydroxyalkyl-alka-1,2-dienephosphonates 1 and 2-diphenylphosphinoyl-2,3-dien-1-ols 2a-c and 3-diphenylphosphinoyl-3,4-dien-2-ols 2d,e, furnishing 3-phosphorylated 2,5-dihydrofurans 3 and 4 in very good yields.
authors.affiliation: Department of Organic Chemistry & Technology, Faculty of Natural Sciences, Konstantin Preslavsky University of Shumen, 115, Universitetska str., BG-9712 Shumen, Bulgaria. vchristo@shu-bg.net.
authors.forename: Valerij Ch
authors.initials: VCh
authors.lastname: Christov
authors.affiliation: Department of Organic Chemistry & Technology, Faculty of Natural Sciences, Konstantin Preslavsky University of Shumen, 115, Universitetska str., BG-9712 Shumen, Bulgaria. iivanov@shu-bg.net.
authors.forename: Ismail E
authors.initials: IE
authors.lastname: Ismailov
authors.affiliation: Department of Organic Chemistry & Technology, Faculty of Natural Sciences, Konstantin Preslavsky University of Shumen, 115, Universitetska str., BG-9712 Shumen, Bulgaria. iivanov@shu-bg.net.
authors.forename: Ivaylo K
authors.initials: IK
authors.lastname: Ivanov
mesh_terms: D000466:Alkadienes / Q000138:chemical synthesis / Q000737:chemistry*; D060326:Chemistry Techniques, Synthetic; D003500:Cyclization; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D007536:Isomerism; D015394:Molecular Structure; D010766:Phosphorylation
chemical_list: D000466:Alkadienes; D005663:Furans