Remarkable rate acceleration of intramolecular Diels-Alder reaction in ionic liquids.
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.
Yanai
Hikaru
H
School of Pharmacy, Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan.
Ogura
Hiroshi
H
Taguchi
Takeo
T
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
D000475:Alkenes; D004952:Esters; D052578:Ionic Liquids; D007783:Lactones; D008670:Metals; D009942:Organometallic Compounds