title: A Diels-Alder approach to the enantioselective construction of fluoromethylated stereogenic carbon centers.
abstract: Highly enantioselective Diels-Alder reactions of β-fluoromethylacrylates were carried out in the presence of a Lewis acid activated chiral oxazaborolidine catalyst. These reactions yielded fluoromethylated cyclohexenes, including trifluoromethyl-, difluoromethyl-, and monofluoromethyl cyclohexenes, as nearly pure enantiomers. The resulting fluoromethyl cyclohexenes were converted into potential synthetic intermediates for bioactive compounds.
authors.affiliation: Department of Environmental and Life Sciences, Toyohashi University of Technology, 1-1 Hibarigaoka, Toyohashi 441-8580, Japan. shiba@ens.tut.ac.jp
authors.forename: Kazutaka
authors.initials: K
authors.lastname: Shibatomi
authors.forename: Fumito
authors.initials: F
authors.lastname: Kobayashi
authors.forename: Akira
authors.initials: A
authors.lastname: Narayama
authors.forename: Ikuhide
authors.initials: I
authors.lastname: Fujisawa
authors.forename: Seiji
authors.initials: S
authors.lastname: Iwasa
mesh_terms: D000179:Acrylates / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry*; D002384:Catalysis; D018360:Crystallography, X-Ray; D053138:Cyclohexenes / Q000737:chemistry; D058116:Lewis Acids / Q000737:chemistry; D008968:Molecular Conformation; D013237:Stereoisomerism
chemical_list: D000179:Acrylates; D053138:Cyclohexenes; D058116:Lewis Acids; D002244:Carbon