title: Preparation and Synthetic Applications of Enantiopure (2S,3S)- or (2R,3S)-2-Halomethyl-1,2-epoxyalkan-3-amines.
abstract: Enantiomerically pure (2S,3S)-3 and its diastereoisomer (2R,3S)-2-halomethyl-1,2-epoxyalkan-3-amine 4 have been obtained from 1-aminoalkyl halomethyl ketones 1 and (iodomethyl)lithium or (chloromethyl)lithium, respectively. Some synthetic applications of compounds 3 are described: chiral unsaturated 1,3-aminoalcohols 8 or 2-(halomethylidene)-3-(dibenzylamino)-alkan-1-ol 11 is obtained from 3 by halogeno-lithium or by hydrogen-lithium exchange, respectively. Transformation of 8c into its methyl ester derivative 9c is also reported.
authors.affiliation: Instituto Universitario de Química Organometálica "Enrique Moles", Universidad de Oviedo, Julián Clavería s/n, 33071 Oviedo, Spain.
authors.forename: José
authors.initials: J
authors.lastname: Barluenga
authors.forename: Beatriz
authors.initials: B
authors.lastname: Baragaña
authors.forename: José M.
authors.initials: JM
authors.lastname: Concellón