title: Regioselective Reversal in the Cyclization of 2-Diazo-3,5-dioxo-6-ynoates (Ynones, Ynamide): Construction of γ-Pyrones and 3(2H)-Furanones Starting from Identical Materials.
abstract: The AgSbF6-catalyzed cyclization of 2-diazo-3,5-dioxo-6-ynoates (ynones, ynamide) in alcoholic solvents affords γ-pyrones, whereas the AgOAc-catalyzed cyclization in 1,2-dichloroethane (DCE) produces 3(2H)-furanones. The cyclization reactions proceeded cleanly under mild reaction conditions, and the desired γ-pyrones or 3(2H)-furanones were obtained in excellent yield. It was observed for the first time that both the catalyst and solvent play key roles in the selective formation. This unique method for the reversal of regioselectivity proved to be highly efficient except for substrates with aliphatic and Me3Si groups at the triple bond position.
authors.affiliation: Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research (Ministry of Education of China), Hunan Normal University , Changsha 410081, China.|Key Laboratory of the Assembly and Application of Organic Functional Molecules, Hunan Normal University , Changsha 410081, China.
authors.forename: Feng
authors.initials: F
authors.lastname: Wang
authors.affiliation: Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research (Ministry of Education of China), Hunan Normal University , Changsha 410081, China.|Key Laboratory of the Assembly and Application of Organic Functional Molecules, Hunan Normal University , Changsha 410081, China.
authors.forename: Shengle
authors.initials: S
authors.lastname: Lu
authors.affiliation: Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research (Ministry of Education of China), Hunan Normal University , Changsha 410081, China.|Key Laboratory of the Assembly and Application of Organic Functional Molecules, Hunan Normal University , Changsha 410081, China.
authors.forename: Bo
authors.initials: B
authors.lastname: Chen
authors.affiliation: Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research (Ministry of Education of China), Hunan Normal University , Changsha 410081, China.|Key Laboratory of the Assembly and Application of Organic Functional Molecules, Hunan Normal University , Changsha 410081, China.
authors.forename: Yali
authors.initials: Y
authors.lastname: Zhou
authors.affiliation: Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research (Ministry of Education of China), Hunan Normal University , Changsha 410081, China.|Key Laboratory of the Assembly and Application of Organic Functional Molecules, Hunan Normal University , Changsha 410081, China.
authors.forename: Ying
authors.initials: Y
authors.lastname: Yang
authors.affiliation: Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research (Ministry of Education of China), Hunan Normal University , Changsha 410081, China.|Key Laboratory of the Assembly and Application of Organic Functional Molecules, Hunan Normal University , Changsha 410081, China.
authors.forename: Guisheng
authors.identifier: 0000-0002-6132-5648
authors.initials: G
authors.lastname: Deng