title: Ring-opening hydrofluorination of 2,3- and 3,4-epoxy amines by HBF4·OEt2: application to the asymmetric synthesis of (S,S)-3-deoxy-3-fluorosafingol.
abstract: Treatment of a range of 2,3- and 3,4-epoxy amines with HBF(4)·OEt(2) at room temperature results in fast and efficient S(N)2-type ring-opening hydrofluorination to give stereodefined amino fluorohydrins. Operational simplicity, scalability, and short reaction time at ambient temperature are notable features of this method. The utility of this methodology is exemplified in a concise asymmetric synthesis of (S,S)-3-deoxy-3-fluorosafingol.
authors.affiliation: Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Oxford, UK.
authors.forename: Alexander J
authors.initials: AJ
authors.lastname: Cresswell
authors.forename: Stephen G
authors.initials: SG
authors.lastname: Davies
authors.forename: James A
authors.initials: JA
authors.lastname: Lee
authors.forename: Melloney J
authors.initials: MJ
authors.lastname: Morris
authors.forename: Paul M
authors.initials: PM
authors.lastname: Roberts
authors.forename: James E
authors.initials: JE
authors.lastname: Thomson