Domino “Staudinger/Semi-Aza-Wittig/Fragmentation” Reactions of γ-Azido-β-hydroxyketones

Treatment of γ-azido-β-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...

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Bibliographic Details
Published in:Journal of organic chemistry 2006-08, Vol.71 (16), p.6165-6170
Main Authors: Freifeld, Ilia, Shojaei, Heydar, Dede, Rüdiger, Langer, Peter
Format: Article
Language:English
Subjects:
Alicyclic compounds
Alicyclic compounds, terpenoids, prostaglandins, steroids
Azides - chemistry
Chemistry
Exact sciences and technology
Hydroxylation
Ketones - chemistry
Molecular Structure
Organic chemistry
Preparations and properties
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Summary:Treatment of γ-azido-β-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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo060891e