title: Domino "Staudinger/semi-aza-Wittig/fragmentation" reactions of gamma-azido-beta-hydroxyketones.
abstract: Treatment of gamma-azido-beta-hydroxyketones with triphenylphosphine resulted, depending on the structural features of the starting materials, in a domino "Staudinger/semi-aza-Wittig/fragmentation" reaction rather than a normal aza-Wittig reaction. 2-Azido-1-hydroxy-1-(2,4-dioxoalkyl)cyclopentanes, readily available by condensation of 1,3-dicarbonyl dianions with 2-azidocyclopentanone, proved to be optimal starting materials for these reactions which afforded 1-(1,3-dioxoalkyl)amino-2-(alkylidene)cyclopentanes.
authors.affiliation: Institut für Biochemie, Universität Greifswald, Soldmannstr. 16, 17487 Greifswald, Germany.
authors.forename: Ilia
authors.initials: I
authors.lastname: Freifeld
authors.forename: Heydar
authors.initials: H
authors.lastname: Shojaei
authors.forename: Rüdiger
authors.initials: R
authors.lastname: Dede
authors.forename: Peter
authors.initials: P
authors.lastname: Langer
mesh_terms: D001386:Azides / Q000737:chemistry*; D006900:Hydroxylation; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure
chemical_list: D001386:Azides; D007659:Ketones