title: Remarkable rate acceleration of intramolecular Diels-Alder reaction in ionic liquids.
abstract: The intramolecular Diels-Alder reaction of an ester-tethered 1,3,9-decatriene system was significantly accelerated in ionic liquids such as [emim]BF(4), [bmim]BF(4) and [bdmim]BF(4). Under the present conditions, the IMDA reaction proceeded smoothly without the use of Lewis acid catalysts to give cis-fused bicyclic lactones in good yield with high diastereoselectivity.
authors.affiliation: School of Pharmacy, Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan.
authors.forename: Hikaru
authors.initials: H
authors.lastname: Yanai
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Ogura
authors.forename: Takeo
authors.initials: T
authors.lastname: Taguchi
mesh_terms: D000475:Alkenes / Q000737:chemistry; D004952:Esters / Q000737:chemistry; D052578:Ionic Liquids / Q000737:chemistry*; D007700:Kinetics; D007783:Lactones / Q000737:chemistry; D008670:Metals / Q000737:chemistry; D009942:Organometallic Compounds / Q000737:chemistry; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: D000475:Alkenes; D004952:Esters; D052578:Ionic Liquids; D007783:Lactones; D008670:Metals; D009942:Organometallic Compounds