title: Organocatalytic Insertion of Isatins into Aryl Difluoronitromethyl Ketones.
abstract: An organocatalytic method that achieves insertion of isatins into aryl difluoronitromethyl ketones under mild conditions is described. The reaction occurs in the presence of 20 mol % of DBU and with 100% atom economy. A series of isatin derived difluoronitromethyl substituted tertiary alcohol benzoates and naphthoates were prepared in 81-99% yield. The general synthetic usefulness of these 3-hydroxyoxindole derivatives is demonstrated with the selective reduction to fluorooximes.
authors.affiliation: Department of Chemistry, Georgetown University , Washington, DC 20057, United States.
authors.forename: Ransheng
authors.initials: R
authors.lastname: Ding
authors.affiliation: Department of Chemistry, Georgetown University , Washington, DC 20057, United States.
authors.forename: Pegah R
authors.initials: PR
authors.lastname: Bakhshi
authors.affiliation: Department of Chemistry, Georgetown University , Washington, DC 20057, United States.
authors.forename: Christian
authors.identifier: 0000-0002-4447-3753
authors.initials: C
authors.lastname: Wolf
mesh_terms: D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods*; D007510:Isatin / Q000737:chemistry*; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure
chemical_list: D007659:Ketones; D007510:Isatin