title: Ammonium-directed oxidation of cyclic allylic and homoallylic amines.
abstract: The ammonium-directed olefinic oxidation of a range of cyclic allylic and homoallylic amines has been investigated. Functionalization of a range of allylic 3-(N,N-dibenzylamino)cycloalk-1-enes with m-CPBA in the presence of Cl(3)CCO(2)H gives exclusively the corresponding syn-epoxide for the 5-membered ring (>99:1 dr), the anti-epoxide for the 8-membered ring (>99:1 dr), and predominantly the anti-epoxide for the 7-membered ring (94:6 dr). Oxidation of the homoallylic amines 3-(N-benzylamino)methylcyclohex-1-ene and 3-(N,N-dibenzylamino)methylcyclohex-1-ene gave, in both cases, the corresponding N-protected 1,2-anti-2,3-syn-3-aminomethylcyclohexane-1,2-diol with high levels of diastereoselectivity (>or=90:10 dr). The versatile synthetic intermediates resulting from these oxidation reactions are readily transformed into a range of amino diols.
authors: Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA, UK.
authors: Christopher W
authors: CW
authors: Bond
authors: Alexander J
authors: AJ
authors: Cresswell
authors: Stephen G
authors: SG
authors: Davies
authors: Ai M
authors: AM
authors: Fletcher
authors: Wataru
authors: W
authors: Kurosawa
authors: James A
authors: JA
authors: Lee
authors: Paul M
authors: PM
authors: Roberts
authors: Angela J
authors: AJ
authors: Russell
authors: Andrew D
authors: AD
authors: Smith
authors: James E
authors: JE
authors: Thomson