Domino "Staudinger/semi-aza-Wittig/fragmentation" reactions of gamma-azido-beta-hydroxyketones.
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.
Freifeld
Ilia
I
Institut für Biochemie, Universität Greifswald, Soldmannstr. 16, 17487 Greifswald, Germany.
Shojaei
Heydar
H
Dede
Rüdiger
R
Langer
Peter
P
D001386:Azides / Q000737:chemistry*; D006900:Hydroxylation; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure
D001386:Azides; D007659:Ketones